Sodium Carbonate → HCID 58504574, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2-amino-6-chloro-4-pyrimidinyl)-2-fluorobenzonitrile (400 mg, 1.61 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (397.0 mg, 2.41 mmol), Pd(PPh3)4 (185 mg, 0.16 mmol), and Na2CO3 (427 mg, 4.02 mmol) in 1,4-dioxane (60 mL) and water (20.0 mL) was stirred and heated at 110° C. for 1 hour under nitrogen. The mixture was cooled to room temperature and concentrated, and the resulting residue was portioned between EtOAc (100 mL) and water (100 mL). The aqueous phase was extracted with EtOAc (2×50 mL), and the combined organic layers were dried Na2CO3, filtered and concentrated to dryness. Purification by SiO2 chromatography using 4:1 petroleum ether/THF as eluent afforded the title compound (190 mg) as a white solid. LC-MS (ES) m/z=334 [M+H]+.

Provenance & Evidence