Ethyl Acetate → HCID 71547824, compound

Participants

Reaction Steps

To a solution of 2-(1-(1H-imidazol-1-yl)propyl)-5-(3-methoxyphenyl) pyridine (0.05 g, 0.17 mmol; prepared as described in Example 7) in dichloromethane (1 mL) was added BBr3 (0.064 g, 0.25 mmol) under nitrogen at 0° C. The reaction was stirred at this temperature for 1 h, allowed to warm to rt and then maintained at rt for another 1 h. The contents were diluted with dichloromethane (100 mL) and then distilled off to obtain crude product. Ice-cold water (100 mL) and dichloromethane (50 mL) were then added to the crude product, the mixture was shaken, and the DCM layer was discarded since the product was in the aqueous layer. To this aqueous layer was added ethyl acetate (100 mL) and saturated sodium bicarbonate solution (150 mL). The organic phase was washed with brine solution (2×50 mL), the layers were separated, and the organic layer was dried over sodium sulphate and distilled off to get the crude product. The product was recrystallized with dichloromethane and hexane to give 3-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)phenol (20 mg, 42% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.59 (s, 1H), 8.78 (d, 1H), 7.99 (d, 1H), 7.92 (s, 1H), 7.36 (d, 2H), 7.26 (t, 1H), 7.09 (d, 1H), 7.08 (s, 1H), 6.95 (s, 1H), 6.81 (d, 1H), 5.38 (q, 1H), 2.33 (m, 2H), 0.81 (t, 3H); LC-MS m/z calcd for [M+H]+ 280.14. found 280.0.

Provenance & Evidence