1,2-Dimethoxyethane → 2-[3-Methoxy-4-(pyridin-3-ylmethyl)phenyl]-1,3-benzoxazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (190 mg, 0.58 mmol), 3-pyridylboronic acid (70 mg, 0.58 mmol), Pd(Ph3P)4 (70 mg, 0.06 mmol), K2CO3 (200 mg, 1.5 mmol), DME (6 mL) and H2O (3 mL) was degassed with bubbling Ar for 15 min. The mixture was heated at 80° C. for 1 h. The reaction was poured into H2O (40 mL) and extracted with CH2Cl2 (2×30 mL). The organic extracts were dried (MgSO4) and concentrated to afford a colorless solid. Purification of the solid by flash chromatography on silica gel (EtOAc:hexanes 3:1) afforded the desired 2-[3-methoxy-4-(pyridin-3-ylmethyl)phenyl]-1,3-benzoxazole as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.56 (br s, 1H), 8.45 (br d, 1H), 7.74–7.80 (m, 3H), 7.50–7.58 (m, 2H), 7.32–7.37 (m, 2H), 7.17–7.24 (m, 2H), 4.00 (s, 2H), 3.93 (s, 3H). MS (ESI) 317 (M+H)+.

Provenance & Evidence