Methanol → Methyl 5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)pyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of the title compound from Step A (0.170 g, 0.628 mmol), Pd(OAc)2 (2.8 mg, 0.013 mmol), Xantphos (0.015 g, 0.025 mmol), methanol (0.254 mL, 6.28 mmol), and triethylamine (8.96 mL, 1.25 mmol) was stirred under an atmosphere of carbon monoxide at 70° C. overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, filtered through Celite using ethyl acetate and concentrated under reduced pressure. Purification by column chromatography on silica gel (30% ethyl acetate in hexanes) provided the title compound: LCMS m/z 250.02 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 9.22 (s, 1 H), 9.00 (s, 1 H), 8.52 (s, 1 H), 3.98 (s, 3 H), 2.94 (br s, 1 H), 1.86 (s, 3 H).

Provenance & Evidence