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

Participants

Reaction Conditions

Reaction Steps

A mixture of the title compound from Step A (1.99 g, 9.21 mmol), palladium acetate (0.041 g, 0.041 Xantphos (0.213 g, 0.368 mmol), methanol (3.73 mL, 92.1 mmol), and triethylamine (18.33 mL, 132.0 mmol) was stirred under an atmosphere of carbon monoxide at 70° C. overnight. The reaction was then cooled to room temperature, diluted with ethyl acetate, filtered through CELITE© and concentrated under reduced pressure. Purification by flash chromatography on silica gel (30% ethyl acetate in hexanes) provided the title compound: LCMS m/z 195.99 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 9.09 (d, J=1.8 Hz, 1 H), 8.92 (d, J=2.2 Hz, 1 H), 8.41 (t, J=2.0 Hz, 1 H), 3.96 (s, 3 H), 2.27 (br s, 1 H), 1.64 (s, 6 H).

Provenance & Evidence