Triethylborane → HCID 24823898, compound

Participants

Reaction Conditions

Reaction Steps

A resealable tube was charged with N-(4-chloro-3-((2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-5-yl)carbamoyl)phenyl)-2,2-difluorobenzo[d][1,3]dioxole-5-carboxamide 38 (0.050 g, 0.080 mmol), palladium(II) acetate (0.0018 g, 0.0080 mmol), 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (0.0066 g, 0.016 mmol), potassium phosphate (0.068 g, 0.32 mmol), and DMF (2.0 mL). A solution of triethylborane (0.12 mL, 0.12 mmol) (1M in THF) was added. The reaction tube was evacuated and purged with argon, and then sealed. The mixture stirred at 100° C. for 6 h. The reaction mixture was filtered through a pad of Celite and concentrated to afford a yellow green solid. This material was purified via preparative thin layer chromatography (eluting three times with 95:5:0.5, dichloromethane/methanol/ammonium hydroxide) to afford N-(4-ethyl-3-((2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-5-yl)carbamoyl)phenyl)-2,2-difluorobenzo[d][1,3]dioxole-5-carboxamide 39 as an off-white solid. MS m/z found 616.2 [MH+]; calc. for C32H31F2N7O4=615.63.

Provenance & Evidence