Boron tribromide → 1054629-49-0

Participants

Reaction Steps

To a stirred solution of [6-fluoro-5-(5-methoxy-benzofuran-2-yl)-pyridin-2-yl]-methyl-carbamic acid tert-butyl ester (66 mg, 0.184 mmol) in dichloromethane (30 mL) at 0° C. under nitrogen atmosphere, BBr3 (1M solution in CH2Cl2, 0.92 mL, 0.92 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight and then cooled to 0° C. Saturated sodium bicarbonate solution was added and the resulting mixture was extracted subsequently with 5% methanol in dichloromethane and with 5% methanol in ethyl acetate. The organic layers were washed with brine separately, dried over Na2SO4, filtered, concentrated and flash chromatographed using 30% ethyl acetate in hexane to give) 2-(2-fluoro-6-methylamino-pyridin-3-yl)-benzofuran-5-ol (19.9 mg) as a off white solid. 1H NMR (400 MHz, METHANOL-d4) δ: 8.02 (m, 1H), 7.27 (d, J=8.59 Hz, 1H), 6.90 (d, J=2.34 Hz, 1H), 6.77 (d, J=3.51 Hz, 1H), 6.70 (dd, J=8.59, 2.34 Hz, 1H), 6.43 (dd, J=8.59, 1.95 Hz, 1H), 2.89 (s, 3H). ESMS: m/z 259.47 [M+1]+

Provenance & Evidence