Diazomethane → 3-bromo-4-cyclopropylpyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-bromo-4-vinylpyridine (Z, 0.4 g, 2.2 mmol) in ether (20 mL) was added palladium acetate (catalytic) and diazomethane (required for preparation, N-nitroso-N-methylurea-1.03 g, 10.0 mmol; 40% potassium hydroxide, 10 mL; ether, 20 mL) portion wise at 0° C. for 10 min. The reaction mixture was stirred at 0° C. for 0.5 h. The reaction mixture was filter through CELITE bed and concentrated under vacuum to afford the crude compound to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ: 8.62 (s, 1H), 8.34-8.33 (d, J=5.2 Hz, 1H), 6.72-6.71 (d, J=4.8 Hz, 1H), 2.25-2.18 (m, 1H), 1.17-1.12 (m, 2H), 0.80-0.76 (m, 2H). MS (M+2): 200.2.

Provenance & Evidence