Potassium Carbonate → HCID 178482360, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-4-iodo-N-methylfuro[2,3-c]pyridin-7-amine (34.0 mg, 0.110 mmol), 1-[4-(tert-butyldimethylsilanyloxy)-cyclohexyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (55.1 mg, 0.136 mmol), (1,1′-bis-(diphenylphosphino)-ferrocene)palladium dichloride (8.6 mg, 0.012 mmol), and potassium carbonate (41.4 mg, 0.300 mmol) in 1,4-dioxane (2.3 mL) and water (0.9 mL) was irradiated under microwave heating at 85° C. for 30 min. Purification by ISCO chromatography (20 to 50% ethyl acetate:heptane) afforded 42.6 mg (82%) of the title compound as a light brown solid. 1H NMR (400 MHz, DMSO-d6): δ 8.15 (s, 1H), 8.07 (s, 1H), 7.84 (s, 1H), 7.36 (s, 1H), 6.88 (q, J=4.55 Hz, 1H), 4.17 (tt, J=3.85, 11.31 Hz, 1H), 3.73 (tt, J=4.01, 10.52 Hz, 1H), 2.91 (d, J=4.55 Hz, 3H), 1.99-2.10 (m, 2H), 1.82-1.97 (m, 4H), 1.38-1.53 (m, 2H), 0.88 (s, 9H), 0.08 (s, 6H); MS (ESI): 461.31, 463.30 [M+H]+; HPLC tR=4.28 min (ZQ3, nonpolar—5 min).

Provenance & Evidence