| Identification | Back Directory | [Name]
tert-butyl 5-bromoindoline-1-carboxylate | [CAS]
261732-38-1 | [Synonyms]
EOS-60873
261732-38-1
N-Boc-5-bromoindoline
1-BOC-5-bromoindoline
1-Boc-5-bromoindoline,97%
tert-butyl 5-bromoindoline-1-carboxylate
tert-Butyl 5-bromo-1H-indoline-1-carboxylate
5-BroMoindole-1-carboxylic Acid tert-Butyl Ester
tert-Butyl 5-bromo-2,3-dihydroindole-1-carboxylate
tert-butyl 5-broMo-2,3-dihydro-1H-indole-1-carboxylate
5-Bromo-1-(tert-butyloxycarbonyl)-2,3-dihydro-1H-indole
1,1-DiMethylethyl 5-broMo-2,3-dihydro-1H-indole-1-carboxylate
5-BroMo-2,3-dihydroindole-1-carboxylic Acid 1,1-DiMethylethyl Ester
1H-Indole-1-carboxylicacid,5-broMo-2,3-dihydro-,1,1-diMethylethylester
5-Bromo-2,3-dihydro-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester | [Molecular Formula]
C13H16BrNO2 | [MDL Number]
MFCD08059280 | [MOL File]
261732-38-1.mol | [Molecular Weight]
298.19 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
tert-Butyl 5-bromoindoline-1-carboxylate is a brominated indoline derivative and a product of biocatalyzed halogenation of nucleobase analogs. It is used in the synthetic preparation of biologic ally active compounds such as selective human β3 adrenergic receptor agonists.
| [Synthesis]
To a solution of 5-bromo-2,3-dihydro-1H-indole (2.11 g, 10.7 mmol) in tetrahydrofuran (THF, 40 mL) was added di-tert-butyl dicarbonate (Boc2O, 2.56 g, 11.7 mmol). The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. Purification of the residue by fast column chromatography (eluent: hexane solution of 8% ethyl acetate) afforded tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylate (2.59 g, 95% yield) as a white solid; mass spectrometry (MS) showed the molecular ion peak (M + H)+ m/z = 298. | [References]
[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3892 - 3909
[2] Patent: US2008/45543, 2008, A1. Location in patent: Page/Page column 28
[3] Patent: US6534535, 2003, B1
[4] Patent: WO2012/103806, 2012, A1. Location in patent: Page/Page column 47
[5] Patent: WO2016/86200, 2016, A1. Location in patent: Page/Page column 300 |
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Alfa Aesar
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