Potassium Phosphate, Tribasic → 3-fluoro-4-{7-methoxy-3-methyl-2-oxo-8-[(E)-2-thiophen-3-ylvinyl]-2,3-dihydroimidazo[4,5-c]quinolin-1-yl}benzonitrile

Participants

Reaction Conditions

Reaction Steps

1-(4-Cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl trifluoromethanesulfonate (119 mg, 240 μmol), 4,4,5,5-tetramethyl-2-[(E)-2-thiophen-3-ylvinyl]-1,3,2-dioxaborolane (142 mg, 602 μmol), tripotassium phosphate (107 mg, 504 μmol) and trans-bis(tricyclohexylphosphine)palladium(II) dichloride (18 mg, 24 μmol) were dissolved in oxygen-free N,N-dimethylformamide (5 ml). The mixture was subsequently heated at 130° C. for 45 min (microwave). The reaction mixture was then filtered with suction, the filtrate was diluted with water and stirred at room temperature for 30 min. The precipitate formed was filtered off with suction and rinsed with water. The residue was chromatographed on flash silica gel (solvent gradient ethyl acetate/0-25% by vol. of ethanol), giving 3-fluoro-4-{7-methoxy-3-methyl-2-oxo-8-[(E)-2-thiophen-3-ylvinyl]-2,3-dihydroimidazo[4,5-c]quinolin-1-yl}benzonitrile (90 mg, 181 μmol) as solid. MS: 457.1 (M+H+), TLC (HPTLC): Rf=0.47 (ethyl acetate/ethanol 2:1, parts by volume).

Provenance & Evidence