ChemicalBook CAS DataBase List 1H-Indole-1,7-dicarboxylic acid, 5-broMo-2,3-dihydro-, 1-(1,1-diMethylethyl) 7-Methyl ester

1H-Indole-1,7-dicarboxylic acid, 5-broMo-2,3-dihydro-, 1-(1,1-diMethylethyl) 7-Methyl ester synthesis

5synthesis methods

Product Name:1H-Indole-1,7-dicarboxylic acid, 5-broMo-2,3-dihydro-, 1-(1,1-diMethylethyl) 7-Methyl ester
CAS Number:860624-87-9
Molecular formula:C15H18BrNO4
Molecular Weight:356.21

1H-Indole-1,7-dicarboxylic acid, 2,3-dihydro-, 1-(1,1-diMethylethyl) 7-Methyl ester

197460-40-5
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1H-Indole-1,7-dicarboxylic acid, 5-broMo-2,3-dihydro-, 1-(1,1-diMethylethyl) 7-Methyl ester

860624-87-9
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$313.00/100mg

Yield:860624-87-9 94%

Reaction Conditions:

with N-Bromosuccinimide in dichloromethane at 20; for 16 h;

Steps:

To a solution of methyl 1,N-(t-butoxycarbonyl)indoline-7-carboxylate (23.5 g, 84.7 mmol) in DCM (300 mL) was added NBS (15.1 g, 84.7 mmol). The mixture was stirred at 20 °C for 16 hours. TLC (petroleum ether : ethyl acetate=5:1, Rf = 0.5) indicated that starting material was consumed completely and a major new spot with lower polarity was detected. The reaction mixture was adjusted to pH = 8 with sat. NaHCO3. The organic phase was separated and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate=1/0 to 5:1) to give methyl 5-bromo-1,N-(t-butoxycarbonyl)indoline-7-carboxylate (28.5 g, 94% yield) as a yellow solid. 1H NMR 400 MHz DMSO = 7.59 (s, 1H), 7.45 (s, 1H), 4.02 (m, 2H), 3.70 (s, 3H), 3.08(m, 2H), 1.43 (s, 9H). ESI-MS (m/z): 356.0 (M+H)+

References:

WO2017/120429,2017,A1 Location in patent:Page/Page column 268