4-Bromo-1-isopropyl-1H-pyrazole → HCID 58266758, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.5M in hexanes, 1.38 mL, 3.45 mmol) was added over 15 min to a solution of 4-bromo-1-isopropyl-1H-pyrazole (500 mg, 2.65 mmol) in diethyl ether (10 mL) at −78° C. After 30 min, a solution of tri-n-butylstannane chloride (920 μL, 3.45 mmol) in diethyl ether (1 mL) was added and the resultant reaction mixture was left to stir at −78° C. for 1 h, then allowed to warm to ambient temperature. The reaction mixture was diluted with diethyl ether (40 mL) and washed with water (20 mL), then brine (20 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford the title product as a colourless oil (98 mg, 94%) which was used without further purification. 1H NMR (CDCl3, 400 MHz): 7.46-7.42 (m, 1H); 7.28 (t, J=4.2 Hz, 1H); 4.59-4.43 (m, 1H); 1.58-1.42 (m, 12H); 1.39-1.24 (m, 6H); 1.02-0.77 (m, 15H).

Provenance & Evidence