Author: Jessica.F

Application of 337536-15-9,Some common heterocyclic compound, 337536-15-9, name is 4-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.

Bromoisoindolin-1-one (11.5 mg, 0.0542 mmol), N-(6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)naphthalen-2-yl)thiophene-3-carboxamide (43.3 mg, 0.114 mmol), Fibercat palladium catalyst (Johnson-Matthey, 21.0 mg), and K2CO3 (2 M in water, 0.1 ml, 0.2 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (0.55 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) for 10 minutes at 50 Watts and 80 C. The reaction was cooled to room temperature, diluted with water (10 ml), and extracted with dichloromethane (6 x 5 ml). The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated. The crude material was washed with 15:1 hexanes / EtOAc and then purified on HPLC (10% -> 95% MeCN / water with 0.1% TFA) to afford title compound (4.9 mg, 24%). MS (ESI pos. ion) m/z: 385 (M+H). Calc’d Exact Mass for C23Hi6N2O2S: 384.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2007/5668; (2007); A2;,
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Application of 99365-40-9, The chemical industry reduces the impact on the environment during synthesis 99365-40-9, name is 6-Bromoindolin-2-one, I believe this compound will play a more active role in future production and life.

To a warm, stirred solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) in 60 mL toluene and 60 mL ethanol was added tetrakis(triphenylphosphine)palladium(0) (2.3 g, 1.9 mmol) followed by 2M aqueous sodium carbonate (50 mL, 100 mmol) and pyridine-3-boronic acid, propanediol ester (5 g, 30.7 mmol). The mixture was stirred at 100 C. in an oil bath for 12 hours. The reaction mixture was cooled, diluted with ethyl acetate (500 mL) and washed with saturated sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to afford a brown solid. The solid was triturated with methylene chloride/diethyl ether to give 2.32 g (42%) of 6-pyridin-3-yl-1,3-dihydro-indol-2-one as a brown solid. 1H NMR (360 MHz, DMSO-d6) delta 10.51 (s, 1H, NH), 8.81 (d, J=2.5 Hz, 1H, Ar-H), 8.55 (dd, J=1.8 and 5.7 Hz, 1H, Ar-H), 8 (m, 1H, Ar-H), 7.45 (dd, J=5.7 and 9.3 Hz, 1H, Ar-H), 7.3 (m, 2H, Ar-H), 7.05 (s, 1H, Ar-H), 3.51 (s, 2H, CH2CO). MS: 210 [M]+.

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-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6689806; (2004); B1;,
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Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-one, 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 16800-68-3, COA of Formula: C10H9NO2

3 – (4 – Fluorophenyl) propyne acid 4 – nitrophenyl-unitz (85.5 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 31 mg and gave rise 65% to unit_.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
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Electric Literature of 3783-77-5, These common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)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.

2. 1-Bromo-4-N-phthalimido-2-butanone 4-N-phthalimido-2-butanone (70.0 g, 0.322 mol) was dissolved in methylene chloride (525 ml) and methanol (425 ml). A solution of bromine (16.5 ml, 0.322 mol) in methanol (100 ml) was added dropwise over a 2 hour period. The reaction mixture was allowed to stir overnight, and was then treated with additional bromine (4 ml, 0.078 mol); after 1 hour, no starting material was visible by TLC. The reaction mixture was concentrated in vacuo to leave a yellow solid, which was triturated with ether and dried under nitrogen to give the product as a white solid, m.p. 88-90 C. (54.84 g, 0.185 mol, 58% yield). 1 NMR (CDCl3): 7.82 (m, 2H), 7.72 (m, 2H), 4.01 (t, J=8 Hz, 2H), 3.93 (s, 2H), 3.12 (t, J=8 Hz, 2H).

Statistics shows that 2-(3-Oxobutyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 3783-77-5.

Reference:
Patent; Pfizer Inc.; US5037834; (1991); A;,
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Synthetic Route of 15362-40-0,Some common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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 finely ground mixture of chromone-3-carboxaldehyde(1 mmol) and oxindole/indolinone (1-(2,6-dichlorophenyl)-2-indolinone)/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1.2 mmol) was irradiated in microwave oven for 1 min and completion of the reaction was monitored with TLC. Reaction mixture was washed with diethyl ether to get pure compounds 5-10.

The synthetic route of 15362-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shaveta; Singh, Amrinder; Kaur, Matinder; Sharma, Surbhi; Bhatti, Rajbir; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 185 – 192;,
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Application of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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: Potassiumhydroxide (0.35 g,6.17 mmol) was added to a solution of 4-aminophthalimide 10 (1.00 g, 6.17 mmol) in dimethylformamide(30 mL) and the mixture was stirred at ambient temperature for 2 h. Iodomethane (0.88 g, 6.17 mmol) wasadded and it was stirred for another 18 h at the same temperature. Water (50 mL) and ethyl acetate (50 mL)was added and the resulting phases were separated. The organic phase was washed with brine, driedover sodium sulfate and concentrated in vacuum. Purification by chromatography on silica gel (Gradient:0-100% ethyl acetate in cyclohexane) afforded the title compound 11a as a yellow solid (1.00 g, 92% yield)

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

Reference:
Article; Fischer, Thomas; Riedl, Rainer; Molecules; vol. 22; 9; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 potassium 1,3-dioxoisoindolin-2-ide (125.0 g, 678.1 mmol) in DMF (500 mL) was added 1-chloropropan-2-one (57 g, 594.0 mmol), the reaction mixture was stirred at ambient temperature for about 60 h. The reaction mixture was poured into ice water (1.0 L), the resulting mixture was stirred for about 1 h. The precipitate was collected by filtration and dried in vacuum to afford the product as a white solid (101.2 g, 8 1.3%). MS (ESI, m/e) [M+1] 203.9.

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

Reference:
Patent; BEIGENE, LTD.; WANG, Zhiwei; GUO, Yunhang; YU, Desheng; (98 pag.)WO2019/34009; (2019); A1;,
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Indoline | C8H9N – PubChem

These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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. name: 5-(Trifluoromethoxy)indoline-2,3-dione

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′-(p-bromophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(p-bromophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5c): Melting point 255-257 C White solid, 97%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.98 (d, J = 3.96 Hz, 1H), 4.56-4.62 (m, 1H), 4.22-4.29 (m, 1H), 3.74 (d, J = 13.2 Hz, 1H), 3.63 (d, J = 16.82 Hz, 1H), 3.37 (d, J = 15.4 Hz, 1H), 2.90 (d, J = 13.96 Hz, 1H), 2.72-2.78 (m, 1H), 2.53 (d, J = 13.92 Hz, 1H), 6.53-6.62 (m, 2H), 6.88-7.55 (m, 21H, Ar); 13C-NMR(CDCl3, 100 MHz): delta/ppm 39.7, 47.3, 52.8, 53.2, 61.4, 67.2, 70.8, 100.8, 110.0, 121.9, 122.4, 122.5, 123.8, 124.3, 126.4, 126.5, 128.5, 128.6, 129.1, 129.2, 130.7, 131.5, 131.7, 131.9, 133.2, 136.2, 136.3, 138.1, 138.4, 138.6, 140.2, 144.6, 179.6, 197.1. EI-MS: m/z 869 (M+). Anal. Calcd for C44H34Br2F3N3O3: C, 60.77; H, 3.94; N, 4.83; Found: C, 60.89; H, 3.81; N, 4.75.

The synthetic route of 5-(Trifluoromethoxy)indoline-2,3-dione has been constantly updated, and we look forward to future research findings.

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);,
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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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromoisoindoline-1,3-dione

Boc2O (2.58 g, 11.82 mmol) was added to a mixture of 5-bromoisoindoline-1,3-dione (2.23 g, 11.26 mmol) in THF (35 mL) at room temperature, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?14% ethyl acetate/hexane) to give tert-butyl 5-bromoisoindoline-2-carboxylate (2.35 g, 7.88 mmol, 70.0%) as a white solid. 1H NMR (300 MHz, CDCl3):delta 1.51(9H,s), 4.58-4.68(4H,m), 7.07-7.17(1H,m), 7.35-7.44(2H,m).

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:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; ODA, Tsuneo; IMADA, Takashi; KONO, Mitsunori; SATO, Ayumu; TOMATA, Yoshihide; OCHIDA, Atsuko; ISHII, Naoki; SASAKI, Yusuke; FUKASE, Yoshiyuki; YUKAWA, Tomoya; FUKUMOTO, Shoji; (200 pag.)EP3192791; (2017); A1;,
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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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Product Details of 7477-63-6

General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25percent, 421 mg, 3.0 mmol) and H2O2 (30percent, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 °C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30percent NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89percent yield).

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yu-Wei; Zheng, Lei; Jia, Feng-Cheng; Chen, Yun-Feng; Wu, An-Xin; Tetrahedron; vol. 75; 11; (2019); p. 1497 – 1503;,
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