Month: May 2021

Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, 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. Recommanded Product: 6-Chloroisatin

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, m.p. 196-198 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6341-92-0, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4556672; (1985); A;; ; Patent; Pfizer Inc.; US4569942; (1986); A;; ; Patent; Pfizer Inc.; US4690943; (1987); A;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1127-59-9, name is 7-Methylindoline-2,3-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 1127-59-9, Quality Control of 7-Methylindoline-2,3-dione

General procedure: Isatin 1 (3 mmol), malononitrile (0.2 g, 3 mmol,), bicyclic CH-acid 2 (3 mmol) and sodium acetate (0.025 g, 0.3 mmol) in ‘solvent-free’ manner or with additive (‘on-solvent’ manner) were grinded with a pestle and mortar at ambient temperature for 15 minutes. After the reaction was finished, the mixture was air-dried. Then the crude solid was put on filter, rinsed with water (2 mL) and EtOH (2 mL), and then dried with a water pump to isolate the spiro-oxindole 3.

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

Reference:
Article; Elinson, Michail N.; Vereshchagin, Anatoly N.; Ryzhkov, Fedor V.; Anisina, Yuliya E.; Arkivoc; vol. 2018; 4; (2018);,
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Related Products of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 25c (2.00 g, 6.94 mmol) and 7a (2.00 g, 10.6 mmol) in THF (70 mL) was added NH4OAc (5.40 g, 70.0 mmol) in MeOH (50 mL). The reaction mixture was stirred at room temperature for 3.5 h. A saturated aqueous solution of NaHCO3 was added to the reaction mixture and extracted with EtOAc three times. The combined organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 60-80percent EtOAc/n-Hexane, on silica gel eluting with 5percent MeOH/CHCl3, and on silica gel eluting with 65percent EtOAc/CHCl3 to afford 2-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione as a pale yellow powder (1.90 g, 60percent): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 0.8 Hz, 3 H), 5.08 (s, 2 H), 6.74 (br s, 1 H), 7.71 – 7.94 (m, 6 H), 8.16 (d, J = 8.5 Hz, 1 H), 9.03 (s, 1 H); MS (ESI) m/z 458 [M+H]+, 30percent, 480 [M+Na]+, 100percent, 456 [M-H]-, 100percent. To a suspension of 2-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione (1.88 g, 4.11 mmol) in EtOH (45 mL) was added hydrazine monohydrate (2.12 g, 42.3 mmol). The reaction mixture was stirred at room temperature for 1 day. MeOH, CHCl3, and NH-silica gel were added to the reaction mixture and concentrated. The residue was purified by column chromatography on NH-silica gel eluting with 5percent MeOH/CHCl3 and on silica gel eluting with 10percent MeOH/CHCl3 to 28percent aqueous ammonia/MeOH/CHCl3 (1/10/100) to afford 1-[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methanamine as a pale yellow amorphous (761 mg, 57percent): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 1.1 Hz, 3 H), 4.12 (s, 2 H), 6.72 (d, J = 1.1 Hz, 1 H), 7.87 (dd, J = 8.5, 1.7 Hz, 1 H), 8.17 (dd, J = 8.5, 0.5 Hz, 1 H), 8.45 (br s, 1 H), 9.03 (s, 1 H); MS (ESI) m/z 328 [M+H]+, 100percent, 326 [M-H]-, 100percent. To a solution of 1-[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methanamine (600 mg, 1.83 mmol) and NEt3 (370 mg, 3.66 mmol) in CHCl3 (15 mL) was added dropwise n-butyryl chloride (0.21 mL, 2.02 mmol) at 0 oC. The reaction mixture was stirred at 0 oC for 0.5 h. Water was added to the reaction mixture and extracted with CHCl3 twice. The combined organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with EtOAc to 10percent MeOH/CHCl3. The amorphous obtained was crystallized from EtOAc/n-Hexane to afford 20 as a yellow powder (441 mg, 61percent): mp 190.0-191.0 oC; 1H NMR (300 MHz, DMSO-d6, delta): 0.89 (t, J = 7.4 Hz, 3 H), 1.47 – 1.63 (m, 2 H), 2.14 (t, J = 7.5 Hz, 2 H), 2.34 (d, J = 0.9 Hz, 3 H), 4.36 (d, J = 5.6 Hz, 2 H), 7.15 (d, J = 0.9 Hz, 1 H), 8.08 (br s, 1 H), 8.14 (d, J = 8.5 Hz, 1 H), 8.34 (br t, J = 5.6 Hz, 1 H), 8.85 (br s, 1 H), 9.43 (s, 1 H), 12.72 (br s, 1 H); MS (ESI) m/z 398 [M+H]+, 100percent, 420 [M+Na]+, 20percent, 396 [M-H]-, 100percent; Anal. Calcd for C19H19N5OS20.2H2O: C, 56.89; H, 4.88; N, 17.46. Found: C, 57.04; H, 4.88; N, 17.17.

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Matsunaga, Yuko; Koami, Takeshi; Asanuma, Hajime; Shiozawa, Fumiyasu; Endo, Mayumi; Ikeda, Akiko; Aoki, Mari; Fujimoto, Natsuko; Wada, Reiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2024 – 2029;,
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Application 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;,
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Synthetic Route of 875003-43-3, These common heterocyclic compound, 875003-43-3, name is 7-Fluoro-1-methylindoline-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.

General procedure: First phenylacetylene (1 mmol) was stirred with Et3N (1 mmol) in CH3CN (5 mL) at roomtemperature. After 15-20 min, N-methyl isatin (1 mmol) and InBr3 (15 mol %)was added and the reaction mixture was stirred for 16-18 h. When N-methylisatin was completely consumed as indicated by TLC, phenyl-N-tosylmethanimine(1 mmol) was added and the reaction mixture was stirred untilthe reaction reached completion, as evidenced by TLC. Acetonitrile wasdistilled out under reduced pressure and the residue was purified by silicagel (mesh 60-120) chromatography (hexane-EtOAc) to afford thecorresponding products. Characterization data of representative compounds.

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Siddiqui; Rahila; Rai, Pragati; Waseem, Malik A.; Abumhdi, Afaf A.H.; Tetrahedron Letters; vol. 56; 29; (2015); p. 4367 – 4370;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 923590-95-8, A common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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: 4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); A1;,
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Reference of 4702-13-0, These common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, 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.

7-b: 1-Bromo-3-phthalimide acetone 2-Phthalimide acetic acid 2.05 g (10.0 mmol), 10 mL of thionyl chloride,Placed in 50mL reaction flask, reflux to the remaining raw materials, vacuum drying, in a brown oil, add 2mL toluene. 15 mL of 50% by weight aqueous solution of KOH was added to 40 mL of diethyl ether, and 6.00 g (33. Mmol) of nitrosourea was slowly added in portions under ice-cooling. After addition, shaking was continued for 10 minutes. , & Lt;And dried for 2 hours in the form of flake KOH to obtain a solution of diazomethane in diethyl ether.The above-mentioned diazomethane-containing ether solution was placed in a 100 mL reaction flask and placed in an ice bath. 2 mL of a toluene solution containing the above oil was slowly added dropwise. The reaction was complete, filtered, rinsed with diethyl ether and the resulting solid spare. The solid was dissolved in 20 mL of tetrahydrofuran, and 2 mL of a 40 wt% aqueous solution of HBr was added dropwise to the reaction mixture, and the mixture was dried under reduced pressure. Add 100mL ethyl acetate, placed in a separatory funnel, respectively, saturated NaHC03, water, saturated NaCl solution, dried anhydrous Mg2S04. Dried under reduced pressure and recrystallized from 95% by weight ethanol to give 1.24 g of a white solid in 44.0% by weight yield.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Union Pharmaceutical Factory; Institute of Materia Medica, Chinese Academy ofMedical Sciences; Pan, Xiandao; Zhang, Peicheng; Yang, Yajun; Zhao, Limin; (20 pag.)CN102786464; (2016); B;,
Indoline – Wikipedia,
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Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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. Recommanded Product: 102359-00-2

Into a 25-mL round-bottom flask was placed tert-butyl 4-aminopiperidine-1- carboxylate (300 mg, 1.50 mmol, 1.00 equiv), dichloromethane (10 mL), 2-oxo-2,3- dihydro-1H-indole-5-carboxylic acid (319 mg, 1.80 mmol, 1.20 equiv), EDCI (344 mg, 1.79 mmol, 1.20 equiv), and HOBT (304 mg, 2.25 mmol, 1.50 equiv). This was followed by the addition of TEA (454 mg, 4.49 mmol, 3.00 equiv) dropwise with stirring at 0oC. The resulting solution was stirred for 14 h at 20oC. The solids were collected by filtration. This resulted in 393 mg (73%) of tert-butyl 4-(2-oxo-2,3-dihydro-1H-indole-5- amido)piperidine-1-carboxylate as a yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 102359-00-2, its application will become more common.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
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Reference of 71294-07-0,Some common heterocyclic compound, 71294-07-0, name is 5,6-Difluoroindolin-2-one, molecular formula is C8H5F2NO, 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.

5,6-difluoro-2,3-dihydro-1H-indole Under an argon atmosphere 0.30 g (1.8 mmol) 5,6-difluoro-1,3-dihydro-indol-2-one were dissolved in 10 mL THF and 3.0 mL of a 1 M borane in THF solution were added dropwise. Then the reaction mixture was heated for 2 h to 70 C. and then cooled. After the addition of 3 mL MeOH a further 5 mL of a 4N aqueous hydrochloric acid solution were added and the mixture was refluxed for 1 h. The organic phase was evaporated down, the aqueous phase was washed with DCM and then made alkaline with a 4N aqueous sodium hydroxide solution and extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, filtered and evaporated down. Yield: 160 mg (47% of theory) ESI-MS: m/z=156 (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 5,6-Difluoroindolin-2-one, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Indoline – Wikipedia,
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These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-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. Recommanded Product: 3,3-Dimethylindolin-2-one

(d) 3,3-Dimethyl-5-nitroindolin-2-one A solution of 22 ml. fuming nitric acid in 200 ml. 80percent sulphuric acid is added dropwise, with cooling, to a solution of 100 g. (0.62 mol) 3,3-dimethylindolin-2-one in 500 ml. 80percent sulphuric acid. The reaction mixutre is then stirred for about 30 minutes, poured on to ice, filtered with suction, washed with water and dried. Yield: 100 g. (78percent of theory); m.p. 192°-196° C. (ethyl acetate/heptane).

The synthetic route of 3,3-Dimethylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Mannheim GmbH; US4666923; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem