Dichloromethane → HCID 58504430, compound

Participants

Reaction Steps

A solution of 2-cyano-3-fluoro-5-{2-(methylamino)-6-[(3R)-3-methyl-4-morpholinyl]-4-pyrimidinyl}phenyl trifluoromethanesulfonate (374 mg, 0.786 mmol), 2-furanylboronic acid (176 mg, 1.572 mmol), PdCl2(dppf).CH2Cl2 adduct (32.1 mg, 0.039 mmol), and K3PO4 (500 mg, 2.358 mmol) in 1,4-dioxane (10 mL) was heated overnight at 100° C. in a sealed tube. The reaction mixture was allowed to cool, then was partitioned between EtOAc (50 mL) and water (50 mL). The aqueous layer was neutralized with 0.1 M HCl (pH paper) and extracted with EtOAc (3×50 mL). The combined organics were dried over Na2SO4, and concentrated. The residue was purified by RP-HPLC (15-50% CH3CN in water, 0.1% TFA). The product fractions were combined, basified with NaHCO3, extracted with EtOAc, dried, and concentrated to afford the title compound (74 mg) as a brown solid LC-MS (ES) m/z=394 [M+H]+.

Provenance & Evidence