Potassium Carbonate → N-(6-(5-carbamoyl-2-methylphenyl)naphthalen-2-yl)thiophene-3-carboxamide

Participants

Reaction Steps

3-bromo-4-methylbenzamide (22.7 mg, 0.106 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (62.5 mg, 0.165 mmol), Fibercat palladium catalyst (Johnson-Matthey, 35.1 mg), and K2CO3 (2 M in water, 0.24 ml, 0.48 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (1.1 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 60 Watts and 80 C for 10 minutes and then for 20 minutes. The reaction was cooled to room temperature, diluted with water (5 ml), extracted with dichloromethane (3×10 ml), diluted with 1,4-dioxane (10 ml), and extracted with EtOAc (3×10 ml). The organic extracts were combined, dried over magnesium sulfate, filtered, concentrated, and purified on HPLC (10%->95% MeCN/water with 0.1% TFA) to afford title compound (3.2 mg, 8%). MS (ESI pos. ion) m/z: 387 (M+H). Calc'd Exact Mass for C23H18N2O2S: 386.

Provenance & Evidence