Ammonium Chloride → HCID 131729447, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ZnBr2 (7.85 g, 34.9 mmol) in THF (40 ml) was added cyclopropylmagnesium bromide (54.8 ml, 27.4 mmol) in THF dropwise at −78° C. After stirring at −78° C. for 30 minutes, the resulting solution was warmed to 0° C. and stirred at 0° C. for 30 minutes. (S)-tert-Butyl-1-(5-bromopyridin-2-yl)ethylcarbamate (Method 27; 3.00 g, 9.96 mmol) and Pd(PPh3)4 (0.576 g, 0.498 mmol) were added successively. The resulting mixture was stirred at 60° C. for 3 hours. After cooled to room temperature, 100 ml of saturated ammonium chloride was added, extracted with EtOAc and dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (hexane-EtOAc=4:1) to give the title compound as a white solid (2.04 g, 78%). 1H NMR (400 MHz) δ 8.30 (d, J=2.0 Hz, 1H), 7.37 (dd, J=1.6 and 8.0 Hz, 1H), 7.25 (d, J=7.6 Hz, 1H), 7.20 (d, J=8.4 Hz, 1H), 4.61 (m, 1H), 1.92 (m, 1H), 1.37 (s, 9H), 1.29 (d, J=7.2 Hz, 3H), 0.96 (m, 2H), 0.69 (m, 2H). MS: Calcd.: 262. Found: [M+H]+263.

Provenance & Evidence