Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, 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 239463-85-5, Safety of (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate

To the Butyl acetate solution of N- alkylated indoline derivative obtained in the reaction step, 35mL of butyl acetate and tartaric acid 1.3 g were added and stirred, and then heated to around 80 C andstirred. After confirming that the tartaric acid was dissolved, then cooled toabout 20 C and stirred for 2 hours. The precipitated solid was collected by filtration, and the resulting wet material was dried under reduced pressure in the vicinity of 40 , to obtain N- alkylated indoline derivative tartrate salt4.6g (purity 96.1%, dialkyl body content 0. 38%) (64.7% yield from the indoline derivative tartrate salt) as a white crystalline.

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, (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOKUYAMA CORPORATION; SHIMIZU, TOMOHIRO; TANAKA, KENJI; (18 pag.)JP2016/3183; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, Formula: C8H8N2O2

Compound II: A mixture of silver sulfate (100 g, 0.32 mol) and iodine (82 g, 0.32 mol) in N,N-dimethylformamide (700 mL) and ethanol (1400 mL) was treated with 5-nitro-2,3-dihydro-1H-indole I (48 g, 0.29 mol). The resulting mixture was stirred at 25 C. for 1.5 h, filtered and the filter pad washed with ethyl acetate. The filtrate was concentrated in vacuo to a volume of approximately 500 mL. This solution was treated with a 1.0 N aqueous sodium thiosulfate solution (100 mL) and a saturated aqueous sodium chloride solution (400 mL). The resulting precipitate was collected by filtration, washed with water and petroleum ether, and dried in vacuo to afford 7-iodo-5-nitro-2,3-dihydro-1H-indole II (83.9 g, 98.9%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) delta 8.18 (d, J=2.20 Hz, 1H), 7.80 (d, J=1.46 Hz, 1H), 7.03 (broad s, 1H), 3.65 (t, J=8.97 Hz, 2H), 3.17 (t, J=8.60 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Patent; Berthel, Steven Joseph; Thakkar, Kshitij Chhabilbhai; US2004/229890; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 5394-18-3 as follows. Computed Properties of C12H12BrNO2

N-(4-Bromobutyl)phthalimide (1.95 g, 6.89 mmol) and sodium iodide (81 mg, 0.537 mmol) were added to a suspension Of K2CO3 (1.64 g, 11.88 mmol) and 1-Boc-piperazine (1.00 g, 5.37 mmol) in acetone (25 mL) and refluxed for 22 h. The reaction mixture was filtered and the solid was washed with acetone (3 x 50 mL). The filtrate was concentrated and the residue purified by column chromatography (hexane:EtOAc, 7:3 to 0:1) to afford 2.08 g (100%) of 58. 1H NMR (500 MHz, CDCl3): delta 7.84 (dd, J = 3.0, 5.4 Hz, 2H), 7.71 (dd, J = 3.0, 5.4 Hz, 2H), 3.71 (t, J = 7.1 Hz, 2H), 3.38-3.43 (m, 4H), 2.32-2.40 (m, 6H), 1.70 (m, 2H), 1.53 (m, 2H), 1.45 (s, 9H); MS (m/z): [M+H]+ 388.4.

According to the analysis of related databases, 5394-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; TALDONE, Tony; RODINA, Anna; PATEL, Pallav; KANG, Yanlong; WO2011/22440; (2011); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 264916-06-5,Some common heterocyclic compound, 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, molecular formula is C13H18N2O2, 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.

Step-1: Synthesis of tert-butyl 5-((1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate To a stirred solution of 1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-indazol-3-one (120 mg, 0.34 mmol, 1.0 eq) in (2.0 mL) of toluene was added m-CPBA (91 mg, 0.37, 1.1 eq) and allowed to stir at rt for 30 minutes. tert-butyl 5-aminoisoindoline-2-carboxylate (102 mg, 408 mmol, 1.2 eq) and DIPEA (0.30 mL, 1.7 mmol, 5.0 eq) were added and allowed to stir at rt for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography to afford the desired product, tert-butyl 5-((1-(2-(tert-butyl)pyridin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate (40 mg, 21.73%) as brown solid.

The synthetic route of 264916-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 169037-23-4, The chemical industry reduces the impact on the environment during synthesis 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(o-tolyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o-methylphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5g): Melting point 229-231 C; white solid, 89%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.96 (d, J = 14.5 Hz, 1H), 4.53-4.62 (m, 1H), 4.21 (d, J = 10.0 Hz, 1H), 3.64 (d, J = 14.00 Hz, 1H), 3.59 (d, J = 15.00 Hz, 1H), 3.37-3.42 (dd, J = 15 Hz, 1H), 2.98-3.02 (dd, J = 14.5 Hz,1H), 2.66-2.71 (m, 1H), 2.48 (d, J = 14.0 Hz, 1H), 2.33 (s, 3H), 2.31 (s, 3H), 6.49-6.58 (m, 2H), 6.99-7.39 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 21.1, 21.5, 39.5, 47.4, 52.8, 52.9, 61.1, 66.9, 70.8, 100.7,109.6, 119.6, 120.9, 121.5, 122.4, 123.9, 124.2, 126.4, 128.4, 128.5, 129.1, 129.3, 129.35, 130.4, 131.6, 133.7, 135.2, 135.8, 136.2, 136.8, 138.2, 138.4, 138.7, 139.6, 139.8. 140.0, 144.3, 179.9, 197.1. EI-MS: m/z 739 (M+). Anal. Calcd for C46H40F3N3O3: C, 74.68; H, 5.45; N, 5.68. Found: C, 74.78; H, 5.51; N, 5.81.

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, 5-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 114041-16-6, The chemical industry reduces the impact on the environment during synthesis 114041-16-6, name is 5,6-Dimethoxyisoindoline, I believe this compound will play a more active role in future production and life.

EXAMPLE 49 2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-2,3-dihydro-5,6-dimethoxy-1H-isoindole A mixture of 1.79 g of 4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene, 3.29 g of 5,6-dimethoxyisoindoline, 25 mL of acetonitrile, and 1.74 mL of N,N-diisopropylethylamine is heated under reflux for 2 days. The reaction is concentrated in vacuo and the black residue partitioned between chloroform and aqueous ammonia. The organic layer is dried (sodium sulfate) and the solvent removed at reduced pressure. Chromatography on silica gel with gradient elution progressing from hexane to chloroform to methyl alcohol, twice, gives 1.34 g of the desired product as a brown gum. MS(Hi res): m/z Calcd for C32 H41 NO4 S 535.2756 Found 535.2723 Calcd for C32 H41 NO4 S H2 O C=69.41, H=7.83, N=2.53, S=5.78 Found C=69.59, H=7.51, N=2.53, S=6.19

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, 5,6-Dimethoxyisoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Powell; Dennis; Paul; Rolf; Hallett; William A.; Berger; Dan M.; Dutia; Minu D.; US5387685; (1995); A;,
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. 84378-94-9, name is 4-Chloro-5-fluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-5-fluoroindoline-2,3-dione

General procedure: To an ethanolic solution of triazole-hydrazide 5 (1.0mmol) was added equimolar amount of substituted Isatin (8a-i) and refluxed overnight at 80C. After completion of the reaction, crude obtained was filtered, washed with water to get Isatin-triazole hydrazones (9a-i) which was purified by column chromatography eluted with acetone: DCM (1:9) to afford the title compounds in moderate to good yield [53].

The synthetic route of 84378-94-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aneja, Babita; Khan, Nashrah Sharif; Khan, Parvez; Queen, Aarfa; Hussain, Afzal; Rehman, Md. Tabish; Alajmi, Mohamed F.; El-Seedi, Hesham R.; Ali, Sher; Hassan, Md. Imtaiyaz; Abid, Mohammad; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 840 – 852;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20780-72-7,Some common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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.

SYNTHETIC PREPARATION 13; Synthesis of 4-bromo-3-(3-hydroxy-6-methoxypyridin-2-yl)-1 ,3-bis( hydroxy methyl )-1 ,3- dihydro-2H-indol-2-one A. Synthesis of 4-bromo-3-hydroxy-3-(3-hvdroxy-6-methoxypyridin-2-yl)-1 ,3- dihydro-2/-/-indol-2-oneTo a pale yellow solution of 6-methoxypyridin-3-ol (7.16 g, 57.2 mmol) in anhydrous tetrahydrofuran (100 ml.) was added isopropylmagnesium chloride (28.6 mL, 57.2 mmol, 2.0 M solution in tetrahydrofuran) at 0 0C. The reaction solution was stirred for 30 min followed by the addition of solid 4-bromoisatin (10.3 g, 45.8 mmol) in portions. The reaction mixture was stirred at ambient temperature for 2 days. The reaction was quenched with 10percent aqueous hydrochloric acid solution (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was triturated with ether to afford 4-bromo-3-hydroxy-3-(3- hydroxy-6-methoxypyridin-2-yl)-1 ,3-dihydro-2H-indol-2-one (10.7 g, 67percent) as a pale yellow solid: mp 172-175 0C; 1H NMR (300 MHz, DMSO-d6) delta 10.61 (s, 1H), 9.41 (s, 1 H), 7.10 (d, J = 8.0 Hz, 2H), 6.99 (d, J = 8.1 Hz, 1 H), 6.81 (d, J = 7.6 Hz, 1 H), 6.77 (br, 1 H), 6.68 (d, J = 8.6 Hz, 1 H), 3.77 (s, 3H); 13C NMR (75 MHz, DMSO-Cf6) delta 176.5, 155.5, 145.9, 139.4, 131.6, 128.9, 127.2, 125.6, 118.9, 111.8, 111.1 , 109.3, 53.8; MS (ES+) mlz 353.2 (M + 1 ), 351.2 (M + 1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromoisatin, its application will become more common.

Reference:
Patent; XENON PHARMACEUTICALS INC.; WO2008/46049; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3485-84-5, These common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, 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.

General procedure: Furan-3-carbaldehyde oxime (2) (300 mg, 2.7 mmol, 1.0 equiv) was mixed with 1-fluoro-4-vinylbenzene (0.39 ml, 3.24 mmol, 1.2 equiv) in dry THF (10 ml). To this mixture, sodium hypochlorite solution (12 ml) was added. Subsequently, the reaction constituents were stirred at room temperature under nitrogen for approximately 16 h. On completion of the reaction, solvent was evaporated. Extraction was carried out using ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated to obtain the crude compound. The latter was then purified by silica gel column chromatography to obtain the pure compound.

Statistics shows that N-Vinylphthalimide is playing an increasingly important role. we look forward to future research findings about 3485-84-5.

Reference:
Article; Balachandran, Sarala; Gadekar, Pradip K.; Parkale, Santosh; Yadav, Vitthal N.; Kamath, Divya; Ramaswamy, Sneha; Sharma, Somesh; Vishwakarma, Ram A.; Dagia, Nilesh M.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 5; (2011); p. 1508 – 1511;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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 5 mL microwave tube was cliargedwimisomdolin-l-one (0.2544 g, 1 .911 mmol), cesium caib onate ( 1.245 g.3.82 mmol) and N-memyl-2-pynOlidinone (9.55 mL) to give a colorless solution. Bmmoa etaldehyde dimethyl acetal ( 1.125 mL, 9 5 mmol) was added . The tu e was sealed, and the reaction mixture was heated in a Eiotage Creabrat 160 *C fcr 60 minutes fined hold time. The reaction mixture was partitioned between ethyl acetate and water. The organic layerwas washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The reaction mixture was purified b y flas h chromatography (20-70 % ethyl acetate :heptane) to provide ab lown oil (0.179 g, 42 % yield).

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem