Potassium Phosphate, Tribasic → HCID 86687621, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 1-(5-CHLORO-2-METHOXYPHENYL)-N-(PYRIMIDIN-4-YL)ISOQUINOLINE-6-SULFONAMIDE (Example 146; 64.66 mg, 0.151 mmol) (3-(trifluoromethyl)phenyl)boronic acid (57.5 mg, 0.303 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (3.11 mg, 7.57 mmol), chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(ii) dichloromethane (11.47 mg, 0.015 mmol), and potassium phosphate (96 mg, 0.454 mmol). The vial was flushed with Ar (g), then 1,4-dioxane (689 μl) and water (68.9 μl) were added in sequence. The vial was sealed and heated in a Biotage Initiator microwave reactor for 30 min at 120° C. The mixture was extracted with EtOAc (4×), and the combined organic extracts were concentrated. The residue was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 3.5% MeOH/DCM) to give 1-(4-methoxy-3′-(trifluoromethyl)-[1,1′-biphenyl]-3-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (35.6 mg, 0.066 mmol, 43.8% yield) as a light-yellow solid. 1H NMR (400 MHz, DMSO-d6) δ=13.02 (br. s., 1H), 8.76-8.64 (m, 2H), 8.57 (s, 1H), 8.25 (d, J=5.8 Hz, 1H), 8.12 (d, J=5.7 Hz, 1H), 8.04-7.90 (m, 4H), 7.83-7.72 (m, 2H), 7.70-7.62 (m, 2H), 7.35 (d, J=8.7 Hz, 1H), 7.03 (d, J=6.0 Hz, 1H), 3.71 (s, 3H). m/z (ESI) 537.2 (M+H)+.

Provenance & Evidence