N-bromobutanimide → 7-Benzyl-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

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Reaction Steps

A mixture of 7-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (302 mg, 1.03 mmole, prepared according to procedures in U.S. Pat. No. 7,928,120 B2 for example 22c) and N-bromosuccinimide (202 mg, 1.13 mmole) in anhydrous dichloromethane (5 ml) was stirred at room temperature for twenty hours before it was quenched with water, extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, concentrated and purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a white solid (259 mg). LC-MS ESI+: 372, 374 (79Br/81Br) (M+1)+; ESI−: 370, 372 (79Br/81Br) (M-b) 7-Benzyl-1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

Provenance & Evidence