Potassium Carbonate → [4-(1,3-Benzoxazol-2-yl)-2-methylphenyl]acetonitrile

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Reaction Conditions

Reaction Steps

A mixture of methane boronic acid (57.6 mg, 0.96 mmol), [4-(1,3-benzoxazol-2-yl)-2-bromophenyl]acetonitrile (example 1) (200 mg, 0.64 mmol), dichlorobis(triphenylphosphine)palladium(II) (22.4 mg, 0.032 mmol), triphenylphosphine (17 mg, 0.064 mmol), and potassium carbonate (177 mg, 1.3 mmol) in degassed DME/H2O (5:1, 12 mL) was heated at 80° C. for 18 h. The mixture was cooled to rt, the two layers were separated and the aqueous layer was extracted with EtOAc (3×). The organics were combined, dried over Na2SO4 and evaporated to dryness to give a brown solid. Purification of the crude solid by flash chromatography on silica gel eluting with a gradient of EtOAc:hexanes (0 to 40 min: 0 to 25% EtOAc) afforded the desired [4-(1,3-benzoxazol-2-yl)-2-methylphenyl]acetonitrile as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.14 (s, 1H), 8.11 (d, 1H), 7.78 (m, 1H), 7.60 (m, 1H), 7.54 (d, 1H), 7.38 (m, 2H), 3.76 (s, 2H), 2.45 (s, 3H). MS (ESI) 249 (M+H)+.

Provenance & Evidence