Category: 22190-33-6

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. 22190-33-6, name is 5-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Bromoindoline

EXAMPLE 489A tert-butyl 5-bromoindoline-1-carboxylate A suspension of 5-bromo-2,3-dihydro-1H-indole (1.0 g, 5.05 mmol) in diethyl ether (50 mL) was treated with di-tert-butyl-dicarbonate (1.32 g, 6.05 mmol), stirred overnight at room temperature and filtered. The filtrate was diluted with hexanes and concentrated in vacuo until crystal formed. The crystals were collected via filtration to give 1.05 g (70% yield) of the desired product. 1H NMR (300 MHz, DMSO-D6) delta ppm 1.50 (s, 9H), 3.06 (t, J=8.82 Hz, 2H), 3.90 (m, 2H), 7.30 (dd, J=8.48, 2.03 Hz, 1H), 7.37 (m, 1H), 7.56 (s, 1H).

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 22190-33-6.

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.; US2005/26944; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 22190-33-6, 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. 22190-33-6, name is 5-Bromoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of the title A compound, 5-bromo-2, 3-DIHYDRO-1 H-INDOLE (15. 75 g, 79.54 mmol) in 200 mL acetonitrile and 200 mL dichloromethane is treated with DMAP (0.971 g, 7.95 mmol) and di-t-butyl dicarbonate (19.14 g, 87.49 MMOL). The solution is stirred at RT for 16 h. The mixture is diluted with 300 mL dichloromethane and washed twice with 1 N aqueous HCI and once with brine, dried over anhydrous MGS04, and concentrated to afford 5-bromo-2,3- dihydro-indole-1-carboxylic acid tert-butyl ester.

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, 5-Bromoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/65351; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 22190-33-6, These common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, 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.

Step 2. tert-Butyl-5-bromoindoline-1-carboxylate (BI12) To a stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in acetonitrile (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2¡Á). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as a off-white solid, which was used in the next step without further purification (3.0 g).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 22190-33-6, These common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, 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.

(i) 5-Bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester To a solution of 600 mg 5-Bromo-2,3-dihydro-1H-indole and 37 mg 4-dimethylaminopyridine in 30 ml acetonitrile was slowly added 992 mg di-tert-butyldicarbonate. After 2 h at 50 C the solvent was removed under reduced pressure. The residue was dissolved in 50 mL ethylacetate and washed with water. The organic solvent was dried over MgSO4 and the solvent was removed under reduced pressure. The product was used without further purification. Yield: 712 mg MS (ES+): m/e= 299.

Statistics shows that 5-Bromoindoline is playing an increasingly important role. we look forward to future research findings about 22190-33-6.

Reference:
Patent; Aventis Pharma Deutschland GmbH; EP1571154; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 22190-33-6, A common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, molecular formula is C8H8BrN, 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-bromoindoline (3.3 g, 16.7 mmol) in DCM (33 mL) at room temperaturewas added 4-dimethylaminopyridine (0.21 g, 1.7 mmol), di-iso-propylethyl amine (4.3 g,33.4 mmol) and di-tert-butyldicarbonate (5.8 g, 26.7 mmol). The resulting mixture was stirred at room temperature for 16 h and then concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 9: 1) to give the title compound (3.63 g, 73%) as a white solid.

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

22190-33-6,Some common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, molecular formula is C8H8BrN, 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.

Step 1: tert-butyl 5-bromoindoline-l-carboxylateTo a solution of 5-bromoindoline (280 mg, 1.41 mmol) in THF (15 mL) and H20 (5 mL) was added k2C03 (293 mg, 2.12 mmol), followed by di-tert-butyl dicarbonate (617 mg, 2.82 mmol) and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and extracted with EtOAc. The combined extract was washed with brine, dried and concentrated to afford desired product (338 mg, 80%). 1H NMR (OMSO-d6): delta 7.59 (1H, br), 7.38 (1H, s), 7.30-7.32 (2H, m), 3.90 (2H, t, / = 8.8 Hz), 3.07 (2H, t, / = 8.8 Hz), 1.50 (9H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22190-33-6, its application will become more common.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; ZHU, Yan; HU, Yuandong; WANG, Huting; LIU, Yuliang; LI, Jijun; SUN, Deguang; WANG, Zhe; WEI, Yongheng; WANG, Zanping; TANG, Guojing; JING, Lutao; WO2012/103806; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem