Potassium Carbonate → HCID 11582026, compound

Participants

Reaction Steps

In a 5 mL microwave reaction vessel was added N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-5-bromo-1H-indazole-3-carboxamide (0.286 mmol), furan-3-boronic acid (0.588 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.0289 mmol), tri-tert-butylphosphine tetrafluoroborate (0.0579 mmol), and potassium carbonate (0.810 mmol). The vessel was evacuated, back-filled with argon gas, and the contents diluted with N,N-dimethylformamide (5.0 mL). The vessel was sealed and subjected to microwave irradiation at 200° C. for 600 s. The contents of the reaction were filtered through Celite (methanol wash) and loaded on a 5 g SCX column. The column was washed with methanol (50 mL) and the product was eluted with 2 M ammonia in methanol and concentrated. The residue was purified by chromatography [1/1 to 0/1 ethyl acetate/(70/30/1 ethyl acetate/methanol/ammonium hydroxide)] followed by preparative HPLC, thus providing the product in 4% yield. 1H NMR (CD3OD) δ 8.51 (s, 1H), 8.35 (s, 1H), 7.93 (s, 1H), 7.70-7.58 (m, 3H), 6.87 (s, 1H), 4.56-4.52 (m, 0.5H), 4.28-4.26 (m, 0.5H), 3.97-3.93 (m, 2H), 2.84 (s, 3H), 2.49-2.12 (m, 8H); LC/MS (EI) tR 4.20 min, m/z 351 (M++1).

Provenance & Evidence