Boron tribromide → HCID 71547910, compound

Participants

Reaction Steps

To a stirred solution of 2-(1-(1H-imidazol-1-yl)ethyl)-5-(4-methoxyphenyl)pyridine (0.075 g, 0.26 mmol; prepared as described for Example 15) in DCM (3 mL) was added BBr3 (0.1 mL 0.4 mmol) at 0° C. The reaction was stirred at rt for about 1 h. The reaction mixture was quenched with saturated NaHCO3 solution (5 mL), diluted with water (100 mL), and extracted with DCM (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120) using 4% methanol in DCM eluent to afford 4-(6-(1-(1H-imidazol-1-yl)ethyl)pyridin-3-yl)phenol as an off-white solid (35 mg, 49% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.62 (s, 1H), 8.74 (d, 1H), 7.99 (dd, 1H), 7.85 (s, 1H), 7.50 (d, 2H), 7.28 (s, 1H), 7.20 (d, 1H), 6.91 (s, 1H), 6.84 (d, 2H), 5.64-5.59 (m, 1H), 1.80 (d, 3H), LC-MS m/z calcd for [M+H]+ 266.12. found 266.2.

Provenance & Evidence