Potassium Carbonate → {2-[3-Bromo-4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

[2-(3-bromo-4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (2.212 mmol, 1 eq), 2-bromo-5-(trifluoromethyl)-pyridine (2.212 mmol, 1 eq) and potassium carbonate (5.531 mmol, 1.5 eq) were suspended in dimethylsulfoxide (25 ml). The reaction mixture was stirred at 60° C. overnight. Reaction mixture was diluted with water (150 ml) and extraction with EtOAc followed (7×15 ml). Organic layers were combined, washed with brine, dried over MgSO4, filtered and evaporated giving {2-[3-bromo-4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (1.734 mmol, yield=78%, purity=93%). [M+H]+=461.29 1H NMR (300 MHz, CDCl3) δ/ppm 1.43 (s, 9H), 2.74-2.84 (m, 2H), 3.29-3.45 (m, 2H), 4.51-4.65 (m, 1H), 7.02-7.15 (m, 2H), 7.16-7.23 (m, 1H), 7.45-7.50 (m, 1H), 7.86-7.95 (m, 1H), 8.35-8.41 (m, 1H)

Provenance & Evidence