Toluene → HCID 71184222, compound

Participants

Reaction Steps

To a solution of methyl 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carboxylate (0.15 g, 0.41 mmol) in 1 ml of THF at −78° C. was added 1M DIBAL-H in toluene (1.03 ml, 1.03 mmol) dropwise. After 5 min, the reaction was allowed to warm to room temperature and stirred for 4 h. Water (0.1 ml), 10% NaOH (0.1 ml) and celite were added to the reaction solution and the mixture was filtered. Washed with THF and the filtrate was dried over Na2SO4, filtered, concentrated and purified by flash chromatography (silica, 20-50% EtOAc/hexanes) to provide {5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methanol as white solid: 1H NMR (400 MHz, CDCl3) δ 8.37 (d, J=2.5 Hz, 1H), 8.05 (m, 2H), 7.56 (dd, J=8.4, 2.5 Hz, 1H), 7.13 (m, 3H), 4.72 (d, J=6.2 Hz, 2H), 2.98 (d, J=6.2 Hz, 1H); LCMS [M+H]+=337.3.

Provenance & Evidence