Hydrogen Bromide → 2-Bromo-1-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)ethanone

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 79b (65 mg, 0.286 mmol) in 50% THF-MeOH (2.4 mL) was added 3N NaOH (95.3 μL, 0.286 mmol). The reaction was stirred overnight and concentrated in vacuo. The residue obtained was azeotroped with toluene (2×5 mL), dried under reduced pressure and slurried in DCM (4 mL). DMF (2.5 μL) was then added, followed by oxalyl chloride (87 μL, 1.00 mmol). The reaction mixture was stirred for 1.5 h and concentrated in vacuo. The resultant solid was dried in vacuo for 30 min and slurried in 4 mL of ACN. The slurry was then treated with trimethylsilyldiazomethane (0.28 mL, 0.57 mmol, 2M hexanes) and allowed to stir for 1 h. The reaction mixture was cooled to 0° C. and HBr (0.11 mL, 0.57 mmol, 5 M acetic acid) was added via syringe. After 30 min of stirring, the reaction mixture was diluted with DCM (50 mL), washed with cold saturated sodium bicarbonate (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give compound 79c which was used without further purification. Mass spectrum (LCMS, ESI pos.) Calcd. For C14H12BrNO 290.0 (M+H). found 290.2.

Provenance & Evidence