Water → Methyl (8-(2-bromoacetyl)quinolin-2-yl)(phenyl)carbamate

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Reaction Steps

A solution of methyl (8-acetylquinolin-2-yl)(phenyl)carbamate (46b; 790 mg) was set stirring in DCM (2 mL) at 0° C. before adding Et3N (190 μl, 1.368 mmol), and TBSOTf (266 μl, 1.158 mmol) sequentially. An additional 3.0 equivalents of Et3N and TBSOTf were then added sequentially After 5 min., the mixture was diluted with sat. aq. NaHCO3, and extracted with DCM. The organic extract was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was dissolved in THF (5 mL) before adding water (303 μL, 16.84 mmol) and Br2 (67.4 μl, 1.316 mmol, Sigma Aldrich). The resulting mixture was stirred at RT for 5 min, then diluted with sat. aq. NaHCO3 and extracted with DCM. The organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The brominated product was used without further purification in the subsequent transformation. m/z (ESI, +ve) 399.1 (M+H)+.

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