Hydrochloric Acid → {5-[4-(tert-Butoxycarbonyl)-2-methylphenyl]-2-methoxypyridin-3-yl}boronic acid

Participants

Reaction Steps

A solution of tert-butyl 4-[6-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]-3-methylbenzoate (INTERMEDIATE 31, 16.0 g, 37.6 mmol), HCl (150 mL, 150 mmol), sodium periodate (24.14 g, 113 mmol) and ethyl acetate (150 mL) was stirred rapidly at room temperature for 1 hour, at which time LCMS showed complete boronate ester hydrolysis. The reaction was diluted with some water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated. The crude was purified by silica gel chromatography to give the title compound. LCMS (M+H)+: 343.95. 1H NMR (500 MHz, CDCl3) δ 8.24 (d, 1H), 8.14 (d, 1H), 7.93 (s, 1H) 7.88 (d, 1H), 7.28 (d, 1H), 5.84 (br, 2H) 4.13 (s, 3H), 2.35 (s, 3H), 1.64 (s, 9H).

Provenance & Evidence