Author: Jessica.F

Synthetic Route of 5428-09-1, 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. 5428-09-1, name is 2-Allylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The optimized hydroformylation?Biginelli reactions were performedby charging an autoclave with [Rh(CO)2acac] (2.60 mg,10.0 mumol 0.25 molpercent), Xantphos (57.9 mg 100 mumol, 2.5 molpercent),and urea (2, 132 mg, 2.2 mmol, 1.1 equiv) as solids under an atmosphereof argon. Subsequently, a solution of the alkene (4 mmol, 2equiv), ethyl acetoacetate (3, 0.25 mL, 260 mg, 2 mmol, 1 equiv)and concd HCl (40 muL) in EtOH (4 mL) was prepared and thentransferred into the autoclave via syringe. The autoclave was purgedthree times with syngas (CO/H2, 1:1), pressurized at 20 bar, andplaced in a preheated aluminum block at 100 °C. The reactions werestopped after 24 h by cooling the autoclave in a water bath (18 °C),venting and purging with argon. To the crude reaction mixture1,3,5-trimethoxybenzene (33.6 mg, 0.20 mmol, 0.1 equiv) as internalstandard was added and the suspension dissolved in CH2Cl2 (5mL). After evaporation of the solvents the crude product was analyzedby NMR spectroscopy and purified via flash chromatographyto yield the pure 3,4-dihydropyrimidin-2(1H)-ones 6a?l as colorlesssolids or foams

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, 2-Allylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fuchs, Daniela; Nasr-Esfahani, Mahboobeh; Diab, Lisa; Smejkal, Tomas; Breit, Bernhard; Synlett; vol. 24; 13; (2013); p. 1657 – 1662;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 20 mL two-necked flask was evacuated and backfilled with molecular oxygen. Then, substrate (1 mmol) and 5 mL of PMAS/Au NPs solution (Au: 0.05 mmol, 5 mol %) were added at room temperature. The mixture was stirred at 80 C under molecular oxygen for 4 h. The reaction mixture was extracted with ethyl acetate. The organic layer was evaporated and examined by 1H NMR analysis (JEOL ECS-400, 400 MHz) with 1,3,5-trimethoxybenzene as an internal standard.

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

Reference:
Article; Amaya, Toru; Ito, Tsubasa; Inada, Yuhi; Saio, Daisuke; Hirao, Toshikazu; Tetrahedron Letters; vol. 53; 45; (2012); p. 6144 – 6147,4;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-45-2, These common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, 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.

To a solution of 6-aminoisoindolin-1-one (0.675 mmol) in 1,2-dichloroethane (0.2 M) was added 2,6-dichloro-4-fluorobenzaldehyde (0.675 mmol), NaBH(OAc)3 (2.025 mmol), and acetic acid (0.675 mmol, 39tL). The mixture was stirred at 80 C for 24 hours. The reaction mixture was quenched with sat.NaHCO3 and extracted with EtOAc. The organic layer was then washed with water and brine, dried over Na2SO4, filtered and evaporated. The crude was purified by preparative HPLC to give the desired compound 300 (Yield = 21%, white cotton). ?H NIVIR (400 1VIHz, DMSO) 8.36 (s, 1H), 7.61 (d, J= 8.6 Hz, 2H), 7.28 (d, J= 8.1 Hz, 1H), 7.05 – 6.82 (m, 2H), 6.02 (t, J 4.9 Hz,1H), 4.40 (d, J= 4.9 Hz, 2H), 4.21 (s, 2H). ?3C NIVIR (101 1VIHz, DMSO) 170.99 (s), 148.98 (s),136.86 (s), 136.74 (s), 133.95 (s), 132.17 (s), 131.24 (s), 124.22 (s), 117.36 (s), 116.88 (s), 116.63 (s), 104.66 (s), 44.75 (s), 43.23 (s).

Statistics shows that 6-Amino-2,3-dihydro-1H-isoindol-1-one is playing an increasingly important role. we look forward to future research findings about 675109-45-2.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 959235-95-1, These common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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.

To a solution of 2-(2-(2-((fe/t-butyldimethylsilyl)oxy)ethoxy)-4-fluorophenyl)-2-((3- methoxy-5-(1 H-1 ,2,4-triazol-1 -yl)phenyl)amino)acetic acid 1f (1 .02 g, 1 .974 mmol) in DMF (10 ml_) were added HATU (1 .13 g, 2.96 mmol), diisopropylethylamine (979 muIota_, 5.92 mmol) and 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (401 mg, 1 .97 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water. The precipitate was filtered off, washed with water and taken up with EtOAc. The organic layer was washed with a 10% solution of K2CO3 in water, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure to give 2-(2-(2-((terf-butyldimethylsilyl)- oxy)ethoxy)-4-fluorophenyl)-2-((3-methoxy-5-(1 H-1 ,2,4-triazol-1 -yl)phenyl)amino)- 1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 3a (1 .34 g). The crude compound was used directly in the next reaction step.

The synthetic route of 959235-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; COESEMANS, Erwin; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; BARDIOT, Dorothee Alice Marie-Eve; (92 pag.)WO2018/178240; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 141452-01-9, These common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, 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.

In the dried Schrank tube, raw porphyrin (0.15 mmol, 32.8 mg), p-toluenesulfonamide (0.3 mmol, 51.1 mg),Iodobenzene acetate (0.15 mmol, 48.3 mg), pentamethylcyclopentadienylphosphonium dichloride (5 mmol%, 4.6 mg), silver triflate (20 mmol%, 7.7 mg),Silver acetate (20 mmol%, 5.1 mg), acetic acid (0.45 mmol, 27 mg)1.5 mL of 1,2-dichloroethane, and the above-mentioned Schalke tube was placed in a 100 o C oil bath.Stir for about 16 h. Stop the reaction and use 2 mLSaturated ammonium chloride is easy to quench the reaction solution.After further extraction with ethyl acetate (4 mL × 5), the organic phases were combined.The solvent was removed on a rotary evaporator. At last,Separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1: 5),Methyl 1-acetyl-7-((4-methylphenyl)sulfonylamino)indoline-5-carboxylate3i (26.1 mg, isolated yield: 45%),This compound was a pale yellow solid.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changzhou University; Sun Song; Dong Yaqun; Cheng Jiang; Yu Jintao; (13 pag.)CN110218172; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3676-85-5, name is 5-Aminoisoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: indolines-derivatives

Example 112 N-(3-Aminobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (182 mg, 0.66 mmol, 1.2 eq) and triethylamine (67 mg, 0.66 mmol, 1.2 eq) were added to a solution of 3-nitrophenylacetic acid (100 mg, 0.55 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (89 mg, 0.55 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 3 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate. The resultant crystal was washed with chloroform/methanol to give a nitro compound (45 mg, 24.1%) containing a minor amount of 4-aminophthalimide as the starting compound. DMF was added to the nitro compound (containing the starting compound, 40 mg, 0.12 mmol). Palladium hydroxide (one small spatula) was added thereto, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60 min. After the completion of the reaction, the reaction solution was filtered through Celite, and washing with ethyl acetate was carried out. Water was then added to the filtrate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure to give the title compound as a crystal (16 mg, 44.4%). MS m/z: 310 1H-NMR delta: 4.17 (2H, d, J = 5.37 Hz), 5.03 (2H, s),6.38 (1H, s), 6.44 (2H, d, J = 7.81 Hz), 6.51 (1H, s), 6.79 (1H, dd, J = 1.95, 8.05 Hz), 6.96 (1H, t, J = 7.68 Hz), 7.60 (1H, dd, J = 1.71, 8.29 Hz), 7.67 (1H, d, J = 8.29 Hz), 7.74 (1H, s), 8.03 (1H, d, J = 1.95 Hz), 11.08 (1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 317-20-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 317-20-4 as follows.

To a stirring solution of7-fluoroindoline-2,3-dione (12.22 g, 74 mmol) inTHF (40 mL) at 0 oc was added phenylmagnesium bromide (148 mL, 148 mmol)dropwise. The reaction mixture was allowed to stir at room temperature after addition20 was completed. The reaction mixture was judged complete by HPLC after 15 min. Thereaction mixture was quenched with saturated NH4Cl and extracted with EtOAc. Thecombined extracts were washed with brine, dried (Na2S04), filtered and concentrated.The residue was purified by silica gel chromatography (EtOAc/hexane) to affordIntermediate A11A(18.84 g, 88%) as yellow solid: HPLC: RT= 1.810 min (H20/MeOH25 with TF A, CHROMOLITH SpeedROD, 4.6x50mm, gradient= 4 min, wavelength=220 nm); MS(ES): m/z = 226 [M+H+-H20]; 1H NMR (400 MHz, DMSO-d6) 8 10.92 (s,lH), 7.37-7.25 (m, 5H), 7.19 (ddd,J=l0.4, 8.1, 1.3 Hz, lH), 7.04-6.92 (m, 2H).

According to the analysis of related databases, 317-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GAVAI, Ashvinikumar V.; ZHAO, Yufen; O’MALLEY, Daniel; QUESNELLE, Claude A.; FINK, Brian E.; NORRIS, Derek J.; HAN, Wen-Ching; DELUCCA, George V.; WO2014/47374; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1201923-48-9, name is (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Safety of (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate

To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro- 2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 mL) at RT was added 4M HCI in dioxane (56 mL, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 mL) affording the title compound (7.8 g, 99%) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1201923-48-9.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/158372; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32372-82-0, name is Isoindoline hydrochloride, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 32372-82-0, Recommanded Product: 32372-82-0

The isoindoline hydrochloride (31.1mg, 0.2mmol),Manganese chloride tetrahydrate (5.9 mg, 0.03 mmol),And a stirrer in the reaction tube,After replacing inert gas,Add 1 ml DMF,Seal the reaction tube.Place the reaction tube in a 150C oil bath reaction pot.Stir the reaction for 10 hours;After cooling to room temperature,Diluted with 15mL water,And extracted three times with ethyl acetate,15mL each time;Combine the extracts,Dry with anhydrous sodium sulfate.After filtration, the filtrate was concentrated under reduced pressure.With ethyl acetate:The crude product was subjected to column chromatography with petroleum ether=1:3 (containing 1% triethylamine) as eluent to obtain a pure product.Black oil, yield 81%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Isoindoline hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Zhang Jingyu; (19 pag.)CN107986927; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41663-84-7, name is 2-Methyl-5-nitroisoindoline-1,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 41663-84-7, HPLC of Formula: C9H6N2O4

EXAMPLE I In a 500 ml three-necked flask equipped with a mechanical stirrer, Dean-Stark trap/condenser, nitrogen inlet, and thermometer was added 25.71 grams (0.20 moles) of p-chlorophenol, 100 ml dimethylsulfoxide, and 150 ml of chlorobenzene. After stirring and nitrogen purging the mixture for 30 min., 15.80 grams of aqueous sodium hydroxide (50.62 wt. %; 0.20 moles) was added. The mixture was heated up to 150 C. with the azeotropic removal of the water of reaction. After the removal of water was complete the temperature was lowered to 60 C. and 41.23 grams (0.20 moles) of 4-nitro-N-methyl phthalimide was added. The mixture was stirred overnight. Upon cooling to room temperature the product precipitated from solution. Filtration, washing the precipitate with water, and recrystallization from isopropanol yielded 50.8 grams of 4-(p-chlorophenyl)-N-methyl phthalimide. The melting point was 131-132 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, 2-Methyl-5-nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; General Electric Company; US4623732; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem