Triethylamine → 2-[3-Methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-benzoxazole

Participants

Reaction Steps

Pyrrolidine (226 μL, 2.83 mmol) was added to a stirring solution of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 0.94 mmol) and triethylamine (390 μL, 2.8 mmol) in CH2Cl2 (5 mL). The mixture was stirred at rt overnight. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford the desired 2-[3-methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 7.82–7.80 (m, 1H), 7.77–7.74 (m, 1H), 7.71 (s, 1H), 7.56–7.50 (m, 2H), 7.35–7.30 (m, 2H), 3.94 (s, 3H), 3.71 (s, 2H), 2.59 (s, 4H), 1.81–1.78 (m, 4H). MS (ESI) 309 (M+H)+.

Provenance & Evidence