Dimethylformamide → HCID 86687675, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 6-(N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-1-(4-fluoro-2-methoxyphenyl)isoquinolin-4-yl trifluoromethanesulfonate (0.140 g, 0.196 mmol), Pd2(dba)3 (0.018 g, 0.020 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.022 g, 0.039 mmol), and zinc cyanide (0.025 ml, 0.392 mmol). DMF (1.962 ml) was added, and the reaction was stirred at 80° C. for one hour. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 12 g, gradient elution 0-50% EtOAc:Heptane). The material was dissolved in DCM and TFA (0.1 ml, 1.298 mmol) was added. The reaction was stirred at room temperature for 30 minutes. The reaction was concentrated and purified via column chromatography (RediSep Gold 12 g, gradient elution 25-100% EtOAc:Heptane) to afford 4-cyano-1-(4-fluoro-2-methoxyphenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=13.06 (br. s., 1H), 9.26 (s, 1H), 8.50 (d, J=1.5 Hz, 1H), 8.06 (dd, J=1.7, 8.9 Hz, 1H), 7.94 (d, J=8.9 Hz, 1H), 7.44 (dd, J=6.8, 8.4 Hz, 1H), 7.32 (d, J=4.6 Hz, 1H), 7.20 (dd, J=2.3, 11.4 Hz, 1H), 7.00 (dt, J=2.4, 8.4 Hz, 1H), 6.92 (d, J=4.6 Hz, 1H), 3.68 (s, 3H). m/z (ESI) 441.2 (M+H)+.

Provenance & Evidence