Indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 3485-84-5, name is N-Vinylphthalimide, 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 3485-84-5, HPLC of Formula: C10H7NO2

General procedure: A magnetically stirred solution of the N-vinylphthalimide (173 mg, 1.00 mmol, 1.0equiv) and xanthate (408 mg, 1.50 mmol, 1.5 equiv) in ethyl acetate (2 mL) wasrefluxed for 15 min under a flow of nitrogen. DLP (10 mol %) was then added to therefluxing solution and the olefin was totally consumed in 90 min. The reactionmixture was then cooled down to room temperature, concentrated under reducedpressure and purified by flash chromatography on silica gel (Et2O/petroleum ether =1:2) to give the desired compound 8b as a white solid (419 mg, 0.94 mmol, 94%yield).

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Reference:
Article; Huang, Qi; Qin, Ling; Zard, Samir Z.; Tetrahedron; vol. 74; 40; (2018); p. 5804 – 5817;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20780-72-7, These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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 4-bromoisatin 30 (100 mg, 0.44 mmol) in degassed THF/water (3:1, 2.5 mL) was added potassium 2-methylphenyltrifluoroborate (114 mg, 0.62 mmol) and K3PO4 (338 mg, 1.59 mmol) followed by Pd(PPh3)2Cl2 (31 mg, 0.04 mmol). The reaction vessel was sealed and heated by microwave irradiation for 4 h at 130 °C. The reaction mixture was cooled to rt, diluted with EtOAc (5 mL) and filtered through Celite®. The organic solution was washed with brine (5 mL) and the resulting aqueous layer was further extracted with EtOAc (2*). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The product was purified via flash column chromatography (eluent 40-60 °C, petrol/EtOAc, 4:1) to afford the title compound (41) as an orange solid (40 mg, 42percent); mp 161-162 °C; numax (solid) 3249, 3017, 2926, 1727, 1603, 1480; deltaH (500 MHz, DMSO-d6) 2.15 (3H, s, CH3), 6.93 (2H, m, C(5)H and C(7)H), 7.14 (1H, d, J = 7.6 Hz, C(6′)H), 7.20-7.26 (1H, m, C(4′)H), 7.30 (1H, d, J = 7.3 Hz, C(3′)H), 7.32-7.37 (1H, m, C(5′)H), 7.56 (1H, app t, J = 7.9 Hz C(6)H), 8.84 (1H, br s, NH); deltaC (125 MHz, DMSO-d6) 19.7, 111.2, 115.7, 125.6, 126.3, 128.6, 128.8, 130.1, 135.7, 136.4, 137.9, 142.8, 149.3, 159.2, 182.0; m/z (ESI-) 236 ([M-H]-, 60percent); HRMS (ESI-) C15H10NO2- ([M-H]-) requires 236.0717; found 236.0719.

Statistics shows that 4-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 20780-72-7.

Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-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. category: indolines-derivatives

The 5-amino-isoindoline-one (Intermediate 8a, 2.1g, 14.2mmoL), acetone (3.5mL, 47.6mmoL) and sodium cyanide (2.1g, 46.8mmoL) was added to 90percent acetic acid (45mL) in.The addition was complete, stirred at room temperature for 48 hours.To the reaction mixture was added water (50mL) and ethyl acetate (100 mL), separated, the organic phase was washed with water (3 × 50 mL), saturated sodium bicarbonate (50 mL), water (50mL), dried over anhydrous magnesium sulfate , filtered, and the solvent was distilled off under reduced pressure, the residue was purified by flash column chromatography, eluent PE: EA = 1: 1, to give a white solid 2.7g, 88percent yield.

The synthetic route of 5-Aminoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; Duan, WenHu; Wan, huixin; Xia, GuangXin; Mei, deCheng; Lin, Yipeng; Liu, Xuejun; Shen, JingKang; (53 pag.)CN103804358; (2016); B;,
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. 13220-46-7, name is 4-Methylindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 13220-46-7

1-(4-Methyl-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one 4-Methyl-1,3-dihydro-indol-2-one was condensed with 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrole-1-carbaldehyde to give the title compound. MS m/z 295.2 [M++1].

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-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. name: tert-Butyl 5-aminoindoline-1-carboxylate

A mixture of 2-isopropoxy-4-methylbenzoic acid (2.57 g), tert-butyl 5-AMINO-1-INDOLINECARBOXYLATE (3.41 g), 1- hydroxybenzotriazole hydrate (2.13 g) and 1- [3- (dimethylamino) PROPYL]-3-ETHYLCARBODIIMIDE (2.16 g) in N, N- dimethylformamide (30 ml) was stirred at ambient temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate and water, and the organic layer was washed with brine and dried over magnesium sulfate. The solvent was concentrated in vacuo and the precipitate was collected by filtration to give tert-butyl 5- [ (2-ISOPROPOXY-4- methylbenzoyl) AMINO]-1-INDOLINECARBOXYLATE (4.82 g). 1H-NMR (DMSO-d6): 8 1. 38 (3H, d, J=6.02 Hz), 1.51 (9H, S), 2.36 (3H, s), 3.07 (2H, t, J=8.36 Hz), 3.91 (2H, t, J=8.36 Hz), 4.75-4. 80 (1H, m), 6.89 (1H, d, J=7.98 Hz), 7.04 (1H, s), 7.41 (1H, s), 7.63-7. 69 (2H, m), 7.71 (1H, d, J=7.98 Hz), 10.01 (1H, s)

The synthetic route of tert-Butyl 5-aminoindoline-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1336963-95-1, A common heterocyclic compound, 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, molecular formula is C8H3BrFNO2, 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.

EXAMPLE 73-(1 ,4′-bipiperidin-1 ‘-ylmethyl)-7-bromo-8-fluoro-//-(1 -phenylcvclopropyl)-2-r3- (trifluorometh l)phenyll-4-quinolinecarboxamide7-bromo-8-fluoro-3-methyl-2-r3-(trifluoromethyl)phenyll-4-quinolinecarboxylic acidTo a solution of 6-bromo-7-fluoro-1 H-indole-2,3-dione (19 g, 77.8 mmol) in THF (200 mL) was added a solution of KOH (21.8 g, 389 mmol) in water (100 mL) dropwise. After the addition was complete, 1-[3-(trifluoromethyl)phenyl]-1 -propanone (15.73 g, 77.8 mmol) was added and the mixture was heated to reflux for 1.5 h. The THF was removed in vacuo, and the remaining aqueous solution was washed with diethyl ether (3 x 100 mL) and acidified with 1 N HCI to pH 2. The precipitate was collected by filtration to afford 7-bromo-8-fluoro-3- methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (16 g, 68% yield).

The synthetic route of 1336963-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl, A.; CHEUNG, Mui; EIDAM, Hilary, S.; FOX, Ryan, M; HILFKER, Mark, A.; MANAS, Eric, S.; YE, Guosen; WO2011/119704; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-79-5,Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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 mixture of 5-nitroindolin-2-one (15 g, 84 mol)in 1,2-dichioroethane (300 mL) was added POBr3 (23 g,80 mmol) . The mixture was heated to 90C and stirred for0.5 h. Then the reaction was cooled just below 90C andimidazole (6.9 g, 101 mmcl) was added in one portion. The mixture was stirred at 90C for 2 h. The reaction was quenched by ice water (200 mL) and then extracted with DCM (200 mL x 3) . The combined organic phase was washed with brine (300 mL x 2), dried over anhydrousNa2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=10:1 to 5:1 to 3:1) to give the title compound (11 g, 46 mmol, 54%yield) as a solid.H NMR (400 MHz, DMSO-d6) oe (ppm) 6.86 (s, 1H), 7.49 (d,J=9.2 Hz, 1H) , 7.91 – 8.07 (m, 1H) , 8.50 (s, 1H) , 12.63(br 5, 1H)

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; NAKAMURA, Tsuyoshi; AKIU, Mayuko; TSUJI, Takashi; TANAKA, Jun; TERAYAMA, Koji; YOKOYAMA, Mika; PINKERTON, Anthony, B.; SESSIONS, Edward, Hampton; (289 pag.)WO2020/10252; (2020); 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 446292-08-6 as follows. category: indolines-derivatives

10 g (0.024 mol) of 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1 ,3-oxazolidin-5- yl}methyl)-1 H-isoindole-1 ,3(2H)-dione (II), 7.12 mL of methylamine (40% aqueous solution, 0.083 mol) and 150 mL of methanol were charged in a 1 L autoclave and heated to reflux temperature (65.0C) for 1 hour. Afterwards, the reaction mass was cooled to 25-30C and transferred to another flask. Then, 9.9 g (0.095 mol) of malonic acid in 50 mL of methanol were added dropwise within 30 min. Then, the reaction mass was stirred to 25-30 C for 24 hours. The solid obtained after filtration was stirred in 100 mL of ethanol at 25 C for 1 hour. Finally, the solid obtained was filtered off and dried under vacuum at 50 C.Yield: 5.9 g. Molar yield: 62.89%. HPLC purity: 99.15%. MP.: 189.14 C (DSC).XRD (2Th): 18.0, 20.1 , 21 .6, 23.0, 24.0, 24.1 , 24.3, and 27.6 as shown in figure 5. IR (cm”1): 3473.0, 2912.5, 2691.9, 1745.6, 1661 .6, 1598.7, 1519.5, 1459.3, 1475.5, 1434.8, 1409.9, 1378.0, 1343.0, 1328.9, 131 1.1 , 1288.9, 1263.3, 1227.1 , 1 162.2, 1 136.7, 1 125.3, 1060.4, 1037.9, 1002.6, 982.6, 919.5, 858.4, 833.0, 777.3, 752.5, 710.8, 689.0, 671.8, 597.5, 556.5, 547.3, 526.1 , 516.0, 505.8, 495.9, 486.1 , 475.3, 465.5 and 455.6 as shown in figure 6. Example

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS LESVI, S. L.; VISHNU NEWADKAR, Ravindranath; CHANGDEO GAIKWAD, Avinash; MADHUKAR HARAD, Ajay; DALMASES BARJOAN, Pere; WO2013/53739; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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. Preparation of (2a) where R3 is 4-chloro To a solution of 4-chlorophthalimide (60 g) in 1 liter of tetrahydrofuran was added borane-methyl sulfide complex (100 ml of 10M), and the mixture was refluxed overnight. After cooling, 100 ml of 6N hydrochloric acid was added slowly, the mixture refluxed for 2 hours, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting aqueous solution washed with ethyl acetate. The aqueous layer was then basified with ammonium hydroxide and extracted with methylene chloride. Solvent was removed from the extract, and the residue distilled under vacuum to give 4-chloroisoindoline, a white solid, m.p. 48-50 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloroisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5726197; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem