(4-Cyano-3-fluorophenyl)boronic acid → HCID 58504779, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of {(2S,5R)-4-[6-chloro-2-(methylamino)-4-pyrimidinyl]-5-methyl-2-morpholinyl}methanol (2.24 g, 7.24 mmol), (4-cyano-3-fluorophenyl)boronic acid (2.64 g, 16.01 mmol), and Pd(PPh3)4 (0.43 g, 0.37 mmol) in 1,4-dioxane (50 mL) and saturated aqueous NaHCO3 (25 mL) was degassed with nitrogen for 10 minutes. It was then stirred at 100° C. under nitrogen for 17 hours, cooled, diluted with water (25 mL) and saturated aqueous NaHCO3 (100 mL), and extracted with EtOAc (3×100 mL). The extracts were washed with brine (150 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (90 g SiO2, 20-100% EtOAc in hexanes gradient) to give the title compound (2.36 g) as a yellow solid. LC-MS (ES) m/z=358 [M+H]+.

Provenance & Evidence