Dimethylformamide → HCID 67340174, compound

Participants

Reaction Steps

Dissolved N1-(3-bromophenyl)-6-methyl-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)isoquinoline-1,5-diamine (0.1125 g, 0.233 mmol) in DMF (0.427 ml, 5.84 mmol) and triethylamine (0.162 ml, 1.16 mmol). Added trimethylsilylacetylene (0.0987 ml, 0.698 mmol) followed by copper (I) iodide (0.00887 g, 0.0465 mmol) and bis(triphenylphosphine)palladium (II) chloride (0.0163 g, 0.0233 mmol). Sealed vessel and stirred reaction mixture at 70° C. After 48 hours, the reaction mixture was diluted with 100 mL water and 100 mL dichloromethane. The layers were separated and the organics washed with 2× water and 2× brine. The organics were dried over sodium sulfate, concentrated in vacuo and purified by column chromatography (20-80% EtOAc/hexanes). The combined fractions of the main peak were concentrated in vacuo to afford 6-methyl-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)-N1-(3-(2-(trimethylsilyl)ethynyl)phenyl)isoquinoline-1,5-diamine as a crystalline solid. MS (M+H)+ 501.2.

Provenance & Evidence