Month: March 2021

Related Products of 7477-63-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5mmol of o-phenylenediamine in turn,5mmol 7-chloro-diketoindoline,6mmol of 2-iodopropane,1mmol p-toluenesulfonic acid,1mmol selective fluorine reagent,20ml of toluene was added to a round-bottomed flask, and the mixture was stirred at 70-90 C under reflux for 48 hours. After the reaction was completed, 30ml of saline was added to quench the reaction. The reaction mixture was extracted with 90ml of ethyl acetate three times. The filtrate was concentrated and separated by column chromatography to obtain analytically pure 7-chloro-6-isopropyl-6H-indole [2,3-b] quinoxaline. Red solid, 91% yield

The synthetic route of 7-Chloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South China Normal University; Guangzhou Huarui Optoelectric Materials Co., Ltd.; Song Xinlong; Zhou Guofu; Pan Junyou; (10 pag.)CN110283177; (2019); A;,
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Synthetic Route of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Pd2(dba)3 (350 mg, 0.38 mmol), XantPhos (540 mg, 0.93 mmol), cesium carbonate (9 g, 27.8 mmol, 2 eq), 6-bromo-isoindolin-1-one (XVII) (2.94 g, 14 mmol, 1 eq) and methyl 6-bromopicolinate (X) (3 g, 14 mmol, 1 eq) were combined in dioxane (100 mL). The mixture was degassed with nitrogen, sealed and heated at 80 C. for overnight. The reaction mixture was poured into water (100 mL). A precipitate formed was filtered and the filtrate was extracted with EtOAc (3*50 mL). The organic extracts were combined and concentrated. The resulting solid was triturated in IPA to give methyl 6-(6-bromo-1-oxoisoindolin-2-yl)picolinate (XVIII) as a solid (3.5 g, 73% yield). 1HNMR (400 MHz, DMSO-d6) delta 3.90 (s, 3H), 5.12 (m, 2H), 7.73 (m, 1H), 7.85 (m, 1H), 7.95 (m, 2H), 8.10 (m, 1H), 8.70 (m, 1H).

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hepatikos Therapeutics, LLC; Smith, Christopher Ronald; Chapman, Justin; US2020/2312; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H3Cl2NO2

General procedure: A solution of C3-beta-cholestrylcarboxylate (4) (1 mmol), proline (11)(1 mmol) and isatin (1a-f)/acenaphthenequinone (7)/ninhydrin (9)(1 mmol) was stirred in aqueous methanol for 1-2 h at reflux temperature.After the completion of reaction as indicated by TLC, methanolwas evaporated under reduced pressure. The crude product waspurified by column chromatography using hexane:EtOAc mixture (2:1)as an eluent.

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Periyasami, Govindasami; Kamalraj, Subban; Padmanaban, Ramanathan; Yeswanth Kumar, Santhakumar; Stalin, Antony; Arumugam, Natarajan; Suresh Kumar, Raju; Rahaman, Mostafizur; Durairaju, Periyan; Alrehaili, Abdulaziz; Aldalbahi, Ali; Bioorganic Chemistry; vol. 88; (2019);,
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Indoline | C8H9N – PubChem

Application of 1074-82-4,Some common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-(4-Aminophenyl)morpholin-3-one (100 gm) was added in n-butanol (300 ml) and charged Alumia sulfonic acid at ambient temperature. Cool the mass, added (R)-Epichlorohydrin (72 gm) and maintain the reaction mass at below 20C. Confirmed the completion of reaction, separated the catalyst. Added sodiumbicarbonate, cool the mass temperature to Q-5C and added methylchloroformate (56 gm) . After completion of reaction, evaporated the n- butanol and charged N,N-dimethylformamide (500 mi), potassium phthalimide (122 gm). The reaction temperature maintained at 95- 100C for 3 hours. Cool the mass temperature to ambient temperature, quenched the mass into water. Filtered the mass and washed the product with water. Dried the material up to get constant weight. The obtained 2-({(5Sj-2-Qxo-3-[4-(3-Gxo-4- morpholmyl]phenyl ]– 1 ,3–oxazol.idm-5–yl}methyl)– 1 H–isoindole– 1 ,3(2H)–d.ione was 186 gm (85% yield) .

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHALANX LABS PRIVATE LIMITED; AVIRNENI, Srirama Krishna; TADIMALLA, Venkata Srihari; GOTTIMUKKULA, Venkata Mallaparaju; MOTAMARRI, N.V. Suryanarayana Murthy; KOTICHUKKALA, Yesubabu; M.S.S., Prakash; SABBAVARAPU, Suribabu; (18 pag.)WO2018/55499; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, molecular formula is C16H20BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C16H20BrNO2

To a solution of 15 (0.4 g, 1.29 mmol) in 20 ml of dry DMF was added 0.75 g (2.31 mmol, 1.8 equiv.) of Cs2C03 and allowed to stir at room temperature for 15 minutes. Then 1.5 g (4.48 mmol, 3.5 equiv.) of bromooctyl phthalamide was added and the reaction mixture was stirred for 2 hrs at room temperature. Solvent was removed under reduced pressure and the residue purified by column chromatography (CH2Cl2:CH3OH:CH3COOH; 20: 1 :0.1) to yield 0.15 g (21 percent) of desired N-9 isomer (120c). lU NMR (500 MHz, CDC13) delta 8.18 (s, 1H), 7.71-7.75 (m, 2H), 7.60-7.64 (m, 2H), 7.21 (m, 3H), 4.13 (t, J= 7.3 Hz, 2H), 3.57 (t, J= 7.2 Hz, 2H), 1.55-1.64 (m, 4H), 1.19- 1.21 (m, 8H); 13C NMR (125 MHz, CDC13) 174.5, 167.6, 153.1, 149.9, 149.6, 144.1, 134.9, 133.0, 132.5, 131.0, 128.1, 127.9, 122.2, 48.9, 43.3, 36.9, 28.6, 27.9, 27.5, 25.7, 25.5. MS (ESI) m/z 569.22/571.13 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17702-83-9, its application will become more common.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; YAN, Pengrong; PATEL, Pallav; PATEL, Hardik J.; TALDONE, Tony; YANG, Chenghua; SUN, Weilin; OCHIANA, Stefan; WO2015/23976; (2015); A2;,
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Indoline | C8H9N – PubChem

Reference of 17564-64-6, These common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

LiHMDS (37 mL of a 1 M solution in THF, 37.0 mmol) was added dropwise to a stirred solution of benzyl 2-methyl-4-oxo-piperidine-1-carboxylate (7.5 g, 30.3 mmol) in THF (150 mL) at -78 C under N2. After 50 minutes, a solution of 2-(chloromethyl)isoindoline-1,3- dione (8.0 g, 40.9 mmol) in THF (30 mL) was added to the reaction mixture over 5 minutes. The solution was stirred for 2 hours then quenched with a saturated aqueous NH4Cl solution. After warming to ambient temperature, the reaction mixture was diluted with EtOAc, washed with saturated aqueous sodium bicarbonate solution and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, 0- 100% EtAOc/PE gradient elution) to give a mixture of benzyl 5-((1,3-dioxoisoindolin-2- yl)methyl)-2-methyl-4-oxopiperidine-1-carboxylate and benzyl 3-((1,3-dioxoisoindolin-2- yl)methyl)-2-methyl-4-oxopiperidine-1-carboxylate (2.4 g). This material was treated with DAST (8 mL, 61 mmol), with cooling in an ice bath. The resulting solution was stirred at 0 C for 15 minutes, then left to warm up to ambient temperature and stirred for 5 hours. The solution was poured carefully, dropwise, onto a stirred mixture of ice/water/NaHCO3/DCM. After 30 minutes, the organic phase was isolated and washed with brine. The organic was dried (Na2SO4), filtered and concentrated in vacuo. The crude mixture was purified by column chromatography (silica, 0- 100% EtOAc-PE gradient elution) give a colourless oil (1.5 g), of which 540 mg was dissolved in ethanol (15 mL) and hydrazine hydrate (100 muL, 2.0 mmol) added. The mixture was heated under relux for 3 hours then cooled to ambient temperature. The resulting suspension was filtered and the filtrate poured directly onto a pre-wetted ion-exchange cartridge. The cartridge was washed with methanol and the product eluted with a 2 M methanolic ammonia solution. The filtrate was concentrated under reduced pressure to give a pale yellow oil (300 mg). This material was dissolved in DCM (3 mL) and Et3N (200 muL, 1.4 mmol) was added under N2. The solution was cooled in an ice bath and methanesulfonyl chloride (100 muL, 1.3 mmol) added. After 5 minutes the cooling bath was removed and the mixture stirred at ambient temperature for 2 hours. The solution was diluted with DCM and saturated aqueous NaHCO3 solution. After stirring for 5 minutes, the organic phase was isolated using a phase separation cartridge. After concentration in vacuo, the residue was purified by column chromatography (silica, 0-100% [10% MeOH in EtOAc]-PE gradient elution) to give a pale yellow oil (150 mg). This material was taken up in DCM (3 mL) and Pd(OAc)2 (40 mg, 0.18 mmol), Et3SiH (150 muL, 0.94 mmol) and Et3N (100 muL, 0.72 mmol) were added. The reaction mixture was stirred at ambient temperature for 1 hour then diluted with MeOH. It was added onto a pre-wetted ion-exchange cartridge. The cartridge was washed with MeOH then the product eluted with a 2 M methanolic NH3 solution. The filtrate was concentrated under reduced pressure to give a brown oil (70 mg) containing a mixture of N-((4,4-difluoro-2- methylpiperidin-3-yl)methyl)methanesulfonamide A58 and N-((4,4-difluoro-6-methylpiperidin- 3-yl)methyl)methanesulfonamide A59, that was taken directly on to the next reaction; MS m/z: 234 (M+H)+.

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 5-Nitroindoline

29: 3-(5-Nitroindolin-1 -yl)phenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside (16)A dry Schlenk tube is charged with Cs2C03 (266 mg, 0.816 mmol, 3 equiv). The tube is evacuated for 30 min and then flushed with argon gas and 3-iodophenyl 2,3,4,6-tetra-O- acetyl-a-D-mannopyranoside 15 (150 mg, 0.272 mmol, 1 equiv) is added to the tube, followed by Pd2(dba)3 (2.8 mg, 0.0027 mmol, 0.01 equiv) and X-Phos (6.5 mg, 0.0136 mmol, 0.05 equiv). The mixture is dissolved in dry dioxane (5 mL). The solvent is degassed in a ultrasonic bath for 20 min. Then 5-nitroindoline (67.3 mg, 0.41 mmol, 1 .5 equiv) is added. The mixture is heated to 80C and stirred for 53 h. TLC (petroleum ether/ EtOAc 3:1 ) and mass spectroscopy helps monitoring the reaction and indicates formation of partially deacetylated mannoside during the progress of the reaction. For that reason dry pyridine (2 mL) and dry acetic anhydride (1 mL) are added 50 h after reaction start to regain fully protected mannoside. Then EtOAc (30 mL) and saturated aqueous NaHC03 solution (50 mL) are added to the reaction mixture. The layers are separated and the organic phase is washed with brine (2 x 50 mL). The aqueous layers are extracted with EtOAc (3 x 30 mL). The combined organic layers are dried with Na2S04, filtered and concentrated under reduced pressure. The residue is purified with silica gelchromatography (petroleum ether/EtOAc, gradient from 10:1 to 1 :1 ). Compound 16 (128 mg, 80%) is obtained as an orange solid.[a]D20 + 59.3 (c = 1 , CHCI3); 1H NMR (CDCI3): delta 2.02 (m, 9H, OAc), 2.20 (s, 3H, OAc), 3.21 (t, J = 8.5 Hz, 2H, CH2), 4.1 1 (m, 4H, CH2, H-6a, H-5), 4.26 (dd, J = 7.3 Hz, 1 H, H-6b), 5.37 (t, J = 9.9 Hz, 1 H, H-4), 5.43 (s, 1 H, H-2), 5.53 (m, 2H, H-1 , H-3), 6.84 (d, J = 8.3 Hz, 1 H, C6H4), 6.98 (m, 3H, C6H4, C6H3), 7.30 (t, J = 8.1 Hz, 1 H, C6H4), 8.00 (s, 1 H, C6H3), 8.05 (d, J = 8.8 Hz, 1 H, C6H3); 13C-NMR (CDCI3): delta 20.89, 20.92, 20.94, (3 OAc), 21.12 (OAc), 27.29 (CH2), 53.36 (CH2), 62.30 (C-6), 66.07 (C-4), 69.01 (C-3), 69.54, 69.56 (2C, C-2, C-5), 96.00 (C-1 ), 106.66, 107.96, 1 1 1.47, 1 14.09, 121.37, 126.13,130.70 (8C, arom. C), 143.38 (1 C, arom. C-O) 152.64, (1 C, arom. C-N), 169.92, 170.23, 170.25, 170.71 (4 C=0)

The synthetic route of 5-Nitroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF BASEL; ERNST, Beat; HEROLD, Janno; WO2011/73112; (2011); A2;,
Indoline – Wikipedia,
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Synthetic Route of 317-20-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

STEP C 2-amino-3-fluoro-benzoic acid A mixture of 19.27 g of the product of Step B and 197 ml of 10N sodium hydroxide solution was heated to 70 C. with stirring and heating was ceased to add 36.5 ml of 30% hydrogen peroxide over 20 minutes during which the temperature rose to 80 C. and descended to 70 C. At the end of the addition, the mixture was heated to 80 C. and held there for 10 minutes and then was cooled during which a mass formed. The latter was added to 200 ml of water with stirring and the pH was adjusted to 1 by addition of concentrated hydrochloric acid at a temperature less than 20 C. The mixture was stirred for 90 minutes and was vacuum filtered. The product was empasted twice with iced water and dried under reduced pressure at 70 C. The product was crystallized from 100 ml of a 1-1 ethanol-water mixture and 3 ml of acetic acid. The mixture was iced for one hour and was vacuum filtered. The product was empasted with a 1-1 ethanol-water mixture and dried at 70 C. under reduced presssure to obtain 14.8 g of 2-amino-3-fluoro-benzoic acid melting at 188 C.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roussel Uclaf; US4486438; (1984); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 21544-81-0, These common heterocyclic compound, 21544-81-0, name is 4,6-Dimethoxyindoline-2,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of 3,5-dimethoxyaniline (199 g, 1.30 mol) in ether (5.0 L) in a 5 L 3-necked flask was cooled to 0C. HCI gas (227 g) was bubbled through the solution over 45 min. After 45 min at 10C, the mixture was filtered, washed with isopropylacetate (4 L), and dried overnight on high vacuum at 45C to give the hydrochloride (242.3 g, 98%), as a white solid. A mixture of the hydrochloride above (20 g, 0.105 mol) and oxalyl chloride (33 mL) in a 3-necked flask equipped with a reflux condenser was heated for 2 h with stirring (170C external temperature), and the oxalyl chloride was distilled from the reaction mixture. The flask was cooled to 0C and methanol (40 mL) was added. The reaction mixture was heated to reflux for 45 min, filtered while hot, and washed with methanol (80 mL) to give the 4,6-dimethoxyisatin (17.2 g, 79%) as a yellow-green solid. To a heated solution (external temp 70C) of the isatin (162 g, 0.78 mol) in aqueous NaOH (40%, 1.5 L) was added H2O2 (35%, 405 mL) slowly over 2 h. After the addition of each portion of H2O2, the internal reaction temperature (initially 64C) increased (to a maximum temp of 80C). After the addition was complete, the foaming reaction mixture was then stirred for an additional 2 h at 70C, and the mixture was allowed to stir overnight while cooling to RT. The mixture was heated to 70C. Additional H2O2 (75 mL) was added, and the mixture was stirred at 70C for a further 2 h until the reaction was complete. After cooling to 10C (bath temperature), aqueous Na2S2O3 (150 mL, saturated) was added. The mixture was brought to pH 8 with HCI (37%, 1.6 L) and pH 6 with acetic acid (glacial, 75 mL), without allowing the reaction mixture to warm to greater than 40C. Filtration of the reaction mixture and washing with water (4 L) gave the expected amino acid as a tan solid (83.7 g, 55%). To a solution of the amino acid (82.7 g, 0.42 mol) in anhydrous THF (4.2 L) was added EDCI (89.2 g, 0.48 mol), HOBT (65 g, 0.48 rnol), and NMM (51.3 mL), and the mixture was allowed to stir at RT for 3 h. Aqueous NH3 (83 mL, 50%) was added, and the mixture was stirred at RT for 16 h. Water (1.25 L) was added, and the mixture was extracted with DCM (2×250 mL). The combined extracts were then washed with water (2×500 mL). Concentration, formation of a slurry with ether (550 mL), filtration, and drying under high vacuum gave 2-amino-4,6-dimethoxybenzamide (46.7 g,57%) as a brown solid. [0111] 2-Amino-4,6-dimethoxy-benzamide (1.06 g, 5.4 mmol), 3,5-dimethyl- 4-hydroxybenzaldehyde (0.810 g, 5.4 mmol), K2CO3 (0.747 g, 5.4 mmol) and I2 (1.645 g, 6.5 mmol) were mixed in DMF (20 ml_) and the reaction mixture was heated at 80C for 12 h. It was cooled to RT and poured into crushed ice. The solid was collected and purified by column chromatography to give 2-(4-hydroxy- 3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4<3H)-one (0.9 g, 51%) as a white solid. Selected data: MP 291-293C. Statistics shows that 4,6-Dimethoxyindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 21544-81-0. Reference:
Patent; Resverlogix Corp.; WO2008/92231; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 58083-59-3, The chemical industry reduces the impact on the environment during synthesis 58083-59-3, name is 6-Chloroisoindolin-1-one, I believe this compound will play a more active role in future production and life.

A mixture of 6-chloro-2, 3-dihydro-isoindol-1-one (0.115 g, 0.68 [MMOL)] and 6M hydrochloric acid (8 ml) in dioxan (1 ml) was heated to [110¡ãC] for 18 hours. After cooling to room temperature the solid was filtered off and dried in vacuo to give the title compound (0.0055g, 4 percent) as a beige solid. 1H-NMR (400 MHz, DMSO): [A] = 4.30 (brs, 2H), 7.58 (dd, 1H), 7.76 (dd, 1H), 8.22 (brs, 3H). LRMS [(ELECTROSPRAY)] : m/z [MH+] 186. Microanalysis : Found: C, 43.13 ; H, 4.05 ; N, 6. 18. [C8H8N02CI.] HCI requires C, 43.26 ; H, 4.08 ; N, 6. [31percent.]

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Chloroisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/14357; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem