Water → HCID 60209930, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 8-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline-2-carboxylate (S1) (130 mg, 0.393 mmol), Cs2CO3 (384 mg, 1.178 mmol), PdCl2(dppf)-CH2Cl2 adduct (32.1 mg, 0.039 mmol) in a microwave tube were added a solution of 4-(chloromethyl)-2-methoxypyridine (124 mg, 0.785 mmol) in THF (3 mL) followed by adding water (0.3 mL). The mixture was heated at 100° C. for 1 h. The reaction was cooled and diluted with EtOAc. The bottom H2O layer was removed. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by reverse-phase HPLC (C-18 column, gradient 5-90% MeCN in H2O with both containing 0.05% TFA) to give methyl 8-fluoro-4-[(2-methoxypyridin-4-yl)methyl]quinoline-2-carboxylate (V4). ES-MS [M+1]+: 327.2.

Provenance & Evidence