Cesium carbonate → 2-[3-methoxy-4-(2H-1,2,3-triazol-2-ylmethyl)phenyl]-1,3-benzoxazole

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Reaction Steps

A slurry of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and 1H-1,2,3-triazole (70 mg, 1.0 mmol), and Cs2CO3 (325 mg, 1.0 mmol) and MeCN (10 mL) was stirred vigorously at rt for 8 h. Silica gel (600 mg) was added, and the reaction mixture was concentrated to dryness. The residue was purified by flash chromatography on silica gel (linear gradient of EtOAc in hexanes from 0 to 100% over 25 min) to afford 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole and 2-[3-methoxy-4-(2H-1,2,3-triazol-2-ylmethyl)phenyl]-1,3-benzoxazole as colorless solids. 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 7.72–7.78 (m, 3H), 7.69 (s, 1H), 7.59 (s, 1H), 7.53–7.56 (m, 1H), 7.31–7.34 (m, 2H), 7.20 (d, 1H), 5.59 (s, 2H), 3.96 (s, 3H). MS (ESI) 307 (M+H). 2-[3-methoxy-4-(2H-1,2,3-triazol-2-ylmethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 7.76–7.80 (m, 3H), 7.68 (s, 1H), 7.56–7.59 (m, 2H), 7.34–7.38 (m, 2H), 7.04 (d, 1H), 5.74 (s, 2H), 3.99 (s, 3H). MS (ESI) 307 (M+H)+.

Provenance & Evidence