Sodium Carbonate → HCID 59526001, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-iodo-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide (300 mg, 0.84 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (619 mg, 2.97 mmol), dichlorobis(triphenylphosphine)palladium (29.3 mg, 0.04 mmol), and sodium carbonate (7.5 mL, 15.0 mmol) in 1,2-dimethoxyethane (7.5 mL) sealed in a 20 mL microwave reaction vessel was purged of oxygen by doing 5 vacuum/argon flush cycles. The reaction solution was heated in a microwave for five minutes at 100° C., and then partitioned between ethyl acetate (50 mL) and water (30 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (12-100% ethyl acetate/hexanes) yielded the title compound.

Provenance & Evidence