Benzonitrile, 4-bromo- → 6-amino-5-bromo-2-(4-cyanophenyl)-N-methylbenzofuran-3-carboxamide

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Reaction Steps

A solution of (6-amino-5-bromo-3-(methylcarbamoyl)benzofuran-2-yl)boronic acid (1 g, 3.19 mmol), 4-bromobenzonitrile (1.17 g, 6.39 mmol), K3PO4.3H2O (1.7 g, 6.39 mmol) and Pd(dppf)Cl2 (40 mg) in dioxane/H2O (10 mL/2 mL) was stirred at 80° C. for 4 h. The mixture was filtered to remove the solid and then the mixture was diluted with water and extracted with EA. The organic layer was washed with brine, dried with Na2SO4 and concentrated. The residue was purified by column chromatography (PE:EA=5:1) to give 6-amino-5-bromo-2-(4-cyanophenyl)-N-methylbenzofuran-3-carboxamide (300 mg, yield: 26%). 1H-NMR (CDCl3, 400 MHz) δ 8.09 (d, J=8.0 Hz, 2H), 7.72 (s, 1H), 7.65 (d, J=8.4 Hz, 2H), 6.84 (s, 1H), 5.84 (s, 1H), 4.28 (s, 2H), 3.00 (d, J=4.4 Hz, 3H). MS (M+H)+: 370/372.

Provenance & Evidence