Potassium Carbonate → HCID 178455335, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,3-dichloro-4-iodo-furo[2,3-c]pyridin-7-ylamine (500 mg, 1.52 mmol), [1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]boronic acid (542 mg, 1.67 mmol) (1,1′-bis-(diphenylphosphine)-ferrocene) palladium dichloride (111 mg, 0.152 mmol) and potassium carbonate (525 mg, 3.80 mmol) in 1,4-dioxane (5.06 mL) and water (2.2 mL) was heated to 75° C. for 2 h. The reaction mixture was concentrated, suspended in ethyl acetate (10 mL), filtered through a pad of Celite, and concentrated onto silica gel. Purification by ISCO chromatography (5 to 50% acetone:heptane) afforded 437 mg (51%) of the title compound as a red-brown solid. 1H NMR (400 MHz, CDCl3) δ 7.84 (s, 1 H), 7.65 (d, J=0.5 Hz, 1 H), 7.57 (d, J=0.8 Hz, 1 H), 5.03 (br. s., 2 H), 3.99-4.41 (m, 1 H), 3.54-3.86 (m, 1 H), 2.14-2.42 (m, 2 H), 2.03 (dd, J=14.4, 3.5 Hz, 2 H), 1.81-1.96 (m, 2 H), 1.45-1.64 (m, 2 H), 0.91 (s, 9 H), 0.05-0.17 (m, 6 H); MS (APCl): 481.31, 483.37 [M+H]+; HPLC tR=3.99 min (ZQ3: nonpolar—4 min).

Provenance & Evidence