(4-Cyano-3-fluorophenyl)boronic acid → HCID 58504784, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2-amino-6-chloro-4-pyrimidinyl)-3-morpholinecarboxamide (390 mg, 1.51 mmol), Pd(PPh3)4 (91 mg, 0.08 mmol), and (4-cyano-3-fluorophenyl)boronic acid (285 mg, 1.73 mmol) in 1,4-dioxane (6 mL) and saturated aqueous NaHCO3 (2 mL) was stirred at 95° C. under argon in a sealed tube for 18 hours. The mixture was cooled, quenched with saturated aqueous NaHCO3 (25 mL) and extracted with EtOAc (3×25 mL). The extracts were washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (34 g, SiO2, CH2Cl2 to 90/10/1 CH2Cl2/CH3OH/NH4OH gradient) to give the title compound (360 mg) as a white solid. LC-MS (ES) m/z=343 [M+H]+.

Provenance & Evidence