Acetic Acid → 2-Bromo-1-(3-(quinolin-2-yl)cyclobutyl)ethanone

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Reaction Steps

A solution of 3-(quinolin-2-yl)cyclobutanecarboxylic acid (200 mg, 0.800 mmol, as prepared above) in DCM was cooled to 0° C. and treated with 10 μL of DMF followed by oxalyl chloride (154 μL, 1.76 mmol). The resulting mixture was stirred at rt for 30 min and concentrated. The residue obtained was dried under reduced pressure for 15 min before being dissolved in CH3CN (5 mL) and treated with 2 M solution of TMSCHN2 in hexanes (0.88 mL, 1.76 mmol). The resulting mixture was stirred for 1 h, cooled to 0° C. and treated with 33 wt % HBr in acetic acid (0.35 mL, 1.76 mmol) dropwise. After stirring for 30 min, the reaction mixture was diluted with DCM (25 mL) and washed with saturated NaHCO3 (2×25 mL). The DCM layer was separated, dried over Na2SO4, filtered, and concentrated. The residue obtained was dried under reduced pressure for 15 min to obtain 2-bromo-1-(3-(quinolin-2-yl)cyclobutyl)ethanone as a viscous oil which was used without further purification in the next step.

Provenance & Evidence