Methanol → 3,5-Dichloro-4-(4-chloro-thiazolo[5,4-c]pyridin-2-yl)-benzaldehyde

Participants

Reaction Steps

A solution of 4-chloro-2-(2,6-dichloro-4-vinyl-phenyl)-thiazolo[5,4-c]pyridine (0.168 g, 0.48 mmol) in DCM (3.8 mL) and MeOH (1 mL) was cooled to −78° C. and degassed with nitrogen then compressed air before the ozone generator was turned on. After 10 minutes, a persistent grey colour remained so the ozone generator was turned off and the reaction mixture was degassed with nitrogen. Triphenylphosphine (0.125 g, 0.48 mmol) was added and the mixture warmed to ambient temperature and stirred for 1 hour. The reaction mixture was partitioned between DCM and water. The organic layer dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0-12% EtOAc in pentane to give the desired compound as an off-white solid (0.138 g, 84% yield). 1H NMR (300 MHz, CDCl3): δ 10.04 (s, 1H), 8.55 (d, J=5.6 Hz, 1H), 7.99-7.98 (m, 3H).

Provenance & Evidence