Sodium Carbonate → N-(6-(1H-indazol-5-yl)naphthalen-2-yl)thiophene-3-carboxamide

Participants

Reaction Steps

5-bromo-1H-indazole (21 mg, 0.087 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (50 mg, 0.13 mmol), Fibercat palladium catalyst (Johnson-Matthey, 2.5 mg), and K2CO3 (2 M in water, 0.25 ml, 0.5 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (2 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 50 Watts and 80 C for 10 minutes. The reaction was then cooled to room temperature, and more Fibercat palladium catalyst (8 mg) was added, along with 2 M Na2CO3 (0.25 ml). The reaction was heated in the microwave at 100 C and 75 Watts for 10 minutes, and then re-cooled to room temperature. The reaction was then diluted with water and methylene chloride, and the organic layer was separated, dried over sodium sulfate, filtered, concentrated, and treated with methylene chloride to afford a precipitate. This suspension was filtered, and the solid was collected to afford the title compound (14 mg, 44%). MS (ESI pos. ion) m/z: 370 (M+H). Calc'd Exact Mass for C22H15N3OS: 369.

Provenance & Evidence