Tag: M.W=100-200

1914-02-9, A common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, molecular formula is C10H13N, 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 3- (chlorosulfonyl) benzoic acid (456 mg, 2.07 mmol, Aldrich) in CH2Cl2 (15 [ML)] was added DMF (15 [UL)] followed by oxalyl chloride (270 [; J, L,] 3.10 mmol). After stirring for 1.5 hours, the solvent and excess oxalyl chloride were removed by rotary evaporation. The residue was dissolved in toluene (15 mL), and [METHYL 2-AMINO-5-CYANOBENZOATE (370 MG,] 2.10 mmol) was added. The mixture was heated in a [105 C] oil bath for 2 hours, and the toluene was then removed by rotary evaporation. The residue was dissolved in [CH2CLZ] (6 mL), and a mixture of 3,3- [DIMETHYLINDOLINE,] descrinbed by Kucerovy et al. in Synth. Commun. 1992, 22 (5), 729- 733, (342 mg, 2.32 mmol) and triethylamine (600 [-LL,] 4.31 mmol) in [CH2C12] (6 [ML)] was added. This mixture was stirred overnight and then added to a separatory funnel with 100 mL of [CH2C12.] This solution was washed with 2 X 100 [ML] of 1 M aqueous HC1 and 100 [ML] of brine. The [CH2CK WAS] evaporated in the presence of silica gel, and the product was purified by chromatography using a Biotage Flash 40 M silica cartridge with a gradient from [CHUCK] to [1 % ETOAC] in [CH2C12 AS] eluent. Yield was 728 mg of white solid as the methyl ester. The methyl ester was hydrolyzed according to method D yielding 292 mg of white [SOLID. 1H] NMR (400 MHz, DMSO-d6) [8 12.] 57 (s, [1] H), 8. [80] (d, [J=] 8.7 Hz, [1 H),] 8.41-8. 44 (m, 2 H), 8.24 (d, [J=] 7.9 Hz, 1 H), 8.09- 8.14 (m, 2 H), 7.83 (t, J= 7.9 Hz, [1] H), 7.55 (d, J= 8.1 Hz, 1 [H),] 7.24 (t, J= 7.7 Hz, 1 H), 7.18 (d, [J=] 7.7 Hz, [1] H), 7.02 (t, [J=] 7.5 Hz, [1 H),] 3.73 (s, 2 H), 1. [08] (s, 6 H).

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

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 solution of isoindolin-1-one (1.00 g, 7.51 mmol) in freshly-distilled THF (25 mL) was added slowly to a suspension of sodium hydride (450 mg, 11.26 mmol, freshly washed with hexane) in THF (25 mL) under N2 at 0 C and stirring was continued (30 min). To the reaction mixture was slowly added ethyl bromoacetate (1.24 mL, 11.26 mmol) and the resulting reaction mixture was allowed to stir at room temperature (16 h). The reaction mixture was quenched with methanol and concentrated. The obtained crude residue was further purified by gravity column chromatography (hexane/ethyl acetate, 2:1) provided pure 1 as an off-white solid (1.39 g, 78%); mp = 77-79C (Lit. mp = 78-80 C)1. 1H NMR (400 MHz, CDCl3) delta 7.87-7.85 (d, J = 7.6 Hz, 1H), 7.57-7.53 (m, 1H), 7.48-7.44 (m, 2H), 4.518 (s, 2H), 4.39 (s, 2H), 4.22 (q, J = 6.8 Hz, 2H), 1.28 (t, J = 6.8 Hz, 3H) ppm. The spectroscopic data was consistent with that previously reported.1

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

Reference:
Article; Patil, Pravin C.; Luzzio, Frederick A.; Ronnebaum, Jarrid M.; Tetrahedron Letters; vol. 58; 38; (2017); p. 3730 – 3733;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-1-one, molecular formula is C8H8N2O, 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. 222036-66-0.

Intermediate 8 (50 mg, 0.162 mmol), 5-amino-2,3-dihydro-isoindol-l-one (72 mg, 0.485 mmol), glacial acetic acid (9 mul, 0.162 mmol) and n-butanol (1.5 ml) were combined and irradiated at 150 0C for 60 minutes in a Biotage 1-60 microwave reactor. The reaction was evaporated, purified by LCMS (low pH buffer) triturated with methanol and dried to give the title compound as a white solid (6 mg, 7percent). 1H NMR (400 MHz, DMSOd6) delta ppm 0.55 – 0.61 (m, 2 H), 0.87 – 0.93 (m, 2 H), 1.50 – 1.57 (m, 1 H), 1.64 – 1.77 (m, 3 H), 1.78 – 1.90 (m, 1 H), 1.91 – 2.00 (m, 2 H), 2.02 – 2.13 (m,2 H), 2.88 – 2.98 (m, 1 H), 3.09 – 3.16 (m, 2 H), 3.28 – 3.56 (m, 2 H), 4.38 (s, 2 H), 7.61 – 7.69 (m,3 H), 7.71 – 7.77 (m, 1 H), 7.86 – 7.91 (m, 1 H), 8.37 – 8.53 (m, 2 H), 10.39 (br. s, 1 H); m/z (ES+APCI)+: 421 [M+H]+.

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

Reference:
Patent; MEDICAL RESEARCH COUNCIL; WO2009/122180; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, Adding some certain compound to certain chemical reactions, such as: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 1074-82-4.

General procedure: To a solution of potassium 1,3-dioxoisoindolin-2-ide (1.85 g, 10.0 mmol), potassium iodide (0.08 g, 0.5 mmol) in acetone (25.0 mL), 1,2-dibromoethane dissolved in acetone (5.0 mL) was added by dropping funnel (3.72 g, 20.0 mmol), refluxed for 10 h. Monitored by TLC, and then filtered, concentrated by vacuum. The crude compound was purified by column chromatography on silica gel to give the desired intermediate 4 2-(2-bromoethyl) isoindoline-1,3-dione (1.83 g, 72.5% yield) as a white solid.

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 1074-82-4.

Reference:
Article; Xie, Ruliang; Mei, Xiangdong; Ning, Jun; Chemical and Pharmaceutical Bulletin; vol. 67; 4; (2019); p. 345 – 350;,
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. 32372-82-0, name is Isoindoline hydrochloride, A new synthetic method of this compound is introduced below., 32372-82-0

1-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (2 eq.) was added to a stirred solution of 7 (1 eq.), isoindoline hydrochloride (1.5 eq.), 1-hydroxybenzotriazole (2 eq.) N,N- diisopropylethylamine (2 eq.) in dichloromethane (150 mL) at 0 C. The resulting solution was stirred at room temperature for 14 h before quenching with saturated sodium bicarbonate solution (120 mL). The organic layer was washed with 1 M hydrochloric acid solution (120 mL) and saturated sodium chloride solution (120 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :4 hexanes/ethyl acetate) to afford 8 (82%) as a white amorphous solid. 1H- NMR (400 MHz, CDC13) delta 7.97 (m, 1H), 7.43 (m, 2H), 7.37 (m, 2H), 6.07 (s, 2H), 6.00 (s, 2H), 4.52 (s, 2H), 4.41 (s, 2H), 3.35 (s, 3H), 3.27 (s, 3H), 3.05 (m, 1H), 1.14 (d, J=7.52, 6H).13C- NMR (100 MHz, CDC13) delta 169.5,157.5, 156.6, 140.0 (2), 130.6, 128.5 (2), 126.2 (2), 126.0, 111.2, 99.9, 95.2, 94.5, 56.1, 55.6 (2), 26.9, 23.6 (2).

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; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

14192-26-8, These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-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.

The 2 – oxo indoline -6 – methyl formate (5g, 0.026 muM), acetic anhydride (20 ml) and the original benzoic acid triethyl ester (29.1g, 0 . 13 muM) are added to a reaction flask, 130 C reaction 6h. The completion of the reaction, the reaction is cooled down to room temperature, filtered, the filter cake is petroleum ether washing, drying, be picture and the solid 7.1g, yield is 75%.

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 14192-26-8.

Reference:
Patent; Shenyang Pharmaceutical University; Qin Mingze; Gong Ping; Zhang Haotian; Zhao Yanfang; (39 pag.)CN106565682; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

222036-66-0, 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.

To a solution of 5-aminoisoindolin-1-one (444 mg, 3 mmol) in 15 mL pyridine was added methylsulfonyl chloride (378 mg, 3.3 mmol), and stirred at room temperature for 4 hours. After the evaporation of the solvent, 1-oxo-5-methylsulfonamidoisoindoline (610 mg) was obtained by silica gel column chromatography. Yield: 90percent. MS m / z [ESI]: 227.0 [M + 1].

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 222036-66-0.

Reference:
Patent; Centaurus BioPharma Co., Ltd.; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XU, Xinhe; SHEN, Yu; XIAO, Dengming; LUO, Hong; PENG, Yong; HAN, Yongxin; ZHANG, Aiming; YANG, Ling; (51 pag.)EP3257857; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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.

[0198] 2,3-Dihydroisoindol-l-one (350 mg, 2.63 mmol), 1,4-bis-bromomethylbenzene (3.78 g, 14.3 mmol), CS2CO3 (3.60 g, 11.1 mmol), in acetonitrile (20 mL), was stirred together at room temperature for 5 hours and 80 C for 20 minutes. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2S04. The solvent was removed under reduced pressure and the product was purified by column chromatography (30% EtOAc/Hexanes) to afford a white solid (410 mg, 49%). .H NMR (300 MHz, CDC13): 6 7.92 (d, 1H), 7.49- 7.55 (m, 2H), 7.37-7.42 (m, 3H), 7.28-7.31 (m, 2H), 4.82 (s, 2.03), 4.49 (s, 2H), 4.31 (s, 2H).

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

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 2058-74-4, name is 1-Methylisatin, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 2058-74-4

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 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, 2058-74-4, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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. 2058-74-4, name is 1-Methylisatin, This compound has unique chemical properties. The synthetic route is as follows., 2058-74-4

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacethylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow soild, 347 mg (66%).

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:
Article; Roh, Hwa Jung; Kim, Su Yeon; Min, Beom Kyu; Kim, Jae Nyoung; Tetrahedron Letters; vol. 58; 1; (2017); p. 21 – 24;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem