5-BROMOINDOLINE

White to brown low melting solid

A) A mixture of 38 g (0.16 mol) of N-acetyl-5-bromoindoline, 31 g of concentrated hydrochloric acid and 41 g of ethanol was charged into a reaction flask and stirred uniformly to obtain the reaction mixture I; B) reaction mixture I at 78 , reaction 4h, the chromatographic monitoring of raw materials disappeared; C) neutralized with 55 g of sodium hydroxide solution; D) to obtain organic phase J and water phase K; E) The organic phase J was extracted three times with 445 g of chloroform. The organic layers were combined and the solvent was recovered to give 30.74 g of 5-bromoindoline, yield 98.04percent and content ≥99percent.Then 20 moles of 5-bromo-N- acetylindoline was dissolved in 40ml of ethanol, to which 25 moles of potassium carbonate solution was added, heated to 75 ~ 80 degrees until the reaction disappeared, and then quenched with water, concentrated , Extracted with dichloromethane, concentrated and crystallized, dried to give compound 5; yield 80percent, product purity 95percent.Example 28Preparation of tert-butyl 5-vinylindoline-1-carboxylate (BI10) Step 1. 5-Bromo-indoline (BI11); To 5-Bromo-1H-indole (2.5 g, 12.82 mmol) in acetic acid (10.0 mL), NaCNBHTo 5-Bromo-1H-indole (2.5 g, 12.82 mmol) in acetic acid (10.0 mL), NaCNBHTo 5-Bromo-1H-indole (2.5 g, 12.82 mmol) in acetic acid (10.0 mL), NaCNBIL (2.38 g, 38.46 mmol) was added portion wise at 10 °C over the period of 20 min. After that the reaction mixture was stirred at RT for 3 h. The reaction mixture was diluted with water and extracted with diethyl ether. The organic layer was washed with saturated NaHCC>3, water and brine solution. The combined ether layer was dried over anhydrous NaTo 5-Bromo-1H-indole (2.5 g, 12.82 mmol) in acetic acid (10.0 mL), NaCNBHExample 28 Preparation of tert-Butyl 5-vinylindoline-1-carboxylate (BI10) Step 1. 5-Bromo-indoline (BI11) To 5-Bromo-1H-indole (2.5 g, 12.82 mmol) in acetic acid (10.0 mL), NaCNBH10 mL of acetic acid was added to 5-bromoindole (2.5 g, 12.8 mmol) and cooled to 0°C. Sodium triacetoxyborohydride(2.38 g, 37.9 mmol) was added thereto, and the mixture was stirred at room temperature for 16 hours. Afteraddition of water, the reaction solution was extracted with Et2O, and the organic layer washed with sodium bicarbonateaqueous solution. The organic layer was dried with MgSO4 and purified by column chromatography to obtain the titlecompound (0.95 g, 38 percent).1H-NMR (CDCl3) δ 7.19 (1H, d), 7.09 (1H, dd), 6.50 (1H, d), 3.74 (1H, brs), 3.56 (2H, t), 3.02 (2H, t)

5-Bromoindoline is a brominated indoline derivative and a product of biocatalyzed halogenation of nucleobase analogs. 5-Bromoindoline is used in the synthetic preparation of biologically active compounds such as selective human β3 adrenergic receptor agonists.

Molecular Weight:198.06
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:196.98401
Monoisotopic Mass:196.98401
Topological Polar Surface Area:12
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes