Author: tianli

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. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., 99365-40-9

Pottasium tert-butoxide (0.085 g, 0.80 mmol) was added to a suspension of 6-bromoindolin-2-one (preparation 1, 3.00 g, 14.2 mmol) in dimethylsulphoxide (7 mL) and, after stirring for 10 minutes at ambient temperature, the mixture was heated to 40-45 C and methyl acrylate (4.00 mL, 44.40 mmol) was added dropwise over 70 minutes. After the addition, the mixture was stirred for 1 hour and then further potassium tert-butoxide (3.82 g, 34.00 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 1.5 hours. Water (45 mL) was added and heating was continued at 85 C for 4 hours and then the mixture was left to cool overnight. The resultant precipitate was filtered and the solid washed with water and hexanes to give the crude product. Recrystallization from ethyl alcohol gave the title compound (1.95 g, 42%) as a white solid. LRMS (m/z): 292/294 (M-1)-. 1H-NMR delta (DMSO-d6): 1.99-2.08 (m, 2H), 2.13-2.22 (m, 2H), 2.41-2.50 (m, 2H), 2.82-2.92 (m, 2H), 7.07 (d, J=3.0 Hz, 1H), 7.21 (dd, J=9.0/3.0 Hz, 1H), 7.50 (d, J=9.0 Hz, 1H), 10.70 (br s, 1H).

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; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
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

6326-79-0, Name is 6-Bromoisatin, 6326-79-0, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Step 1: Preparation of 6-bromo-1H-indazole-3-carboxylic acid The solution of 6-bromoisatin (10 g, 22 mmol) in 1N aqueous NaOH solution (48 Ml) was stirred at 50 C. for 1 h. The mixture was cooled to 0 C. Sodium nitrite (3 g, 22 mmol) solution in water (11 Ml) was added dropwise for 15 min at 0 C. The mixture was added to the solution of water (90 Ml) and sulfuric acid (4.6 Ml) at 0 C. for 15 min. The mixture was added to the solution of conc. hydrochloric acid (40 Ml) and SnCl2.2H2O (24 g, 53 mmol). After 1 h, the mixture was filtered and washed with water. The solid was dried through air flow to give the titled compound (8.98 g). 1H NMR (300 MHz, DMSO-d6) delta 13.76 (bs, 1H), 7.87 (s, 1H), 7.55 (d, J=8 Hz, 1H), 7.27 (d, J=8 Hz, 1H), 2.44 (s, 3H).

Statistics shows that 6-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 6326-79-0.

Reference:
Patent; Sim, Tae Bo; Son, Jung Beom; Kim, Hwan; Park, Dong Sik; Choi, Hwan Geun; Ham, Young Jin; Hah, Jung Mi; Yoo, Kyung Ho; Oh, Chang Hyun; Lee, So Ha; Ha, Jae Du; Cho, Sung Yun; Kwon, Byoung Mog; Han, Dong Cho; US2012/130069; (2012); 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

A common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, 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. 32372-82-0.

1-Ethyl-3- (3-dimethylaminopropyl)carbodiimide (1.63 g, 8.54 mmol, 2.0 eq.) was added to a stirred solution of S14 (950 mg, 4.27 mmol, 1 eq.), isoindoline hydrochloride (731 mg, 4.70 mmol, 1.1 eq.), 1-hydroxybenzotriazole (635 mg, 4.70 mmol, 1.1 eq.) N-,N-diisopropylethylamine (3.26 mL, 18.8 mmol, 4.4 eq.) in dichloromethane 42 mL) at 0 C. The resulting solution was stirred at rt for 14 h before quenching with saturated sodium bicarbonate solution (30 mL). The organic layer was washed with 1 M hydrochloric acid solution (30 mL) and saturated sodium chloride solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Si02, 3 : 10 hexanes/ethylacetate) to afford S15 (1.22 g, 91.8%) as a white amorphous solid. 1H NMR (400 MHz, CDC13) delta 10.47 (s, 1H), 7.48 – 7.21 (m, 5H), 7.15 (d, J= 7.4 Hz, 1H), 5.01 (s, 2H), 4.58 (s, 2H), 4.02 – 3.76 (m, 4H), 1.32 (d, J= 6.8 Hz, 7H).13C NMR (100 MHz, CDC13) delta 190.8, 167.6, 153.7, 144.9, 136.4, 136.4, 134.4, 132.5, 128.0, 127.7, 126.1, 123.3, 122.7, 111.2, 56.1, 53.4, 52.3, 27.3, 24.4 (2). HRMS (ESI+) m/z [M + Na+] calcd for C20H21NO3Na, 346.1419, found 346.1404.

The synthetic route of Isoindoline hydrochloride has been constantly updated, and we look forward to future research findings.

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

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 923590-95-8 name is 4-Bromoisoindoline hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 923590-95-8

Step e. TEA (126 ml, 903 mmol) was added drop-wise over 5 min to a stirred suspension of 4- bromoisoindoline HQ (100 g, 430 mmol) in THF (700 ml) and the mixture was cooled to 10C. The cooled mixture was then treated with a solution of di-tert-butyl dicarbonate (122 g, 559 mmol) in THF (300 ml) over 15 min whilst maintaining the temperature below 20C, and the resulting mixture was stirred at rt for 12 h. The reaction was concentrated under vacuum to give an oil, which was partitioned between EtOAc (600 ml) and water (600 ml). The aqueous phase was collected and extracted with EtOAc (2 chi 500 ml), and the combined organic extracts were washed with brine, dried over Na2S04, filtered and evaporated to dryness under vacuum to give the crude product as a solid (161 g). The crude solid was slurried in hexane (150 ml), filtered and the resulting solid washed with hexane (60 ml) before being dried under vacuum at rt to give the desired product as a solid (95.7 g, 75%). LCMS (Method R): rt 3.02 min, m/z 242 (-tBu)/198(-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) delta ppm 7.51-7.46 (dd, J = 7.8, 0.6 Hz, 1H), 7.38-730 (m, 1H), 7.29-7.21 (m, 1H), 4.73- 4.63 (d, 2H), 4.56-4.47 (d, 2H), 1.50-1.42 (d, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisoindoline hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem