Potassium Phosphate, Tribasic → HCID 86687483, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 1-(4-chloro-2-methoxyphenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (53.42 mg, 0.125 mmol), (3-cyanophenyl)boronic acid (55.2 mg, 0.375 mmol), potassium phosphate (106 mg, 0.501 mmol), and chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) methyl-t-butylether adduct (Strem Chemical, Newburyport, Mass.) (9.52 mg, 0.013 mmol). The vial was flushed with Ar (g), then 1,4-dioxane (501 μl) and water (125 μl) were added. The vial was sealed and heated to 120° C. for 30 min in a microwave reactor. The mixture was extracted with EtOAc (3×). The combined organic extracts were concentrated. The crude product was purified by chromatography on silica gel (0 to 10% MeOH/DCM) to give 1-(3′-cyano-3-methoxy-[1,1′-biphenyl]-4-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (37.15 mg, 0.075 mmol, 60.2% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm=13.00 (br. s., 1H), 8.70 (d, J=5.7 Hz, 1H), 8.66 (d, J=1.4 Hz, 1H), 8.58 (s, 1H), 8.37 (d, J=1.6 Hz, 1H), 8.30-8.17 (m, 2H), 8.15-8.05 (m, 1H), 8.01-7.94 (m, 1H), 7.92-7.86 (m, 1H), 7.81-7.70 (m, 2H), 7.60-7.43 (m, 3H), 7.03 (d, J=6.5 Hz, 1H), 3.78 (s, 3H); m/z (ESI) 494.2 (M+H)+.

Provenance & Evidence