2-Bromopropane → 5-Bromo-1-isopropylpyridin-2(1H)-one

Participants

Reaction Steps

Potassium tert-butoxide (16.80 g, 18.63 mL, 142.2 mmol) was added to a suspension of 5-bromo-1H-pyridin-2-one (25 g, 142.2 mmol) in DME (247.5 mL) and the mixture stirred at ambient temperature for 30 minutes. To the mixture was added potassium carbonate (13.76 g, 99.54 mmol) and 2-bromopropane (34.98 g, 26.70 mL, 284.4 mmol) and the reaction mixture heated at reflux for 64 hours. The reaction mixture was filtered to remove the resultant precipitate and the filtrate concentrated in vacuo. The residue was recrystalised from DCM/hexane to give the sub-title product as an off-white solid (19.1 g 62% Yield). 1H NMR (400.0 MHz, CDCl3) δ 1.36 (d, 6H), 5.22 (dt, 1H), 6.49 (d, 1H), 7.31 (dd, 1H) and 7.41 (d, 1H) ppm; MS (ES+) 217.3.

Provenance & Evidence