Dimethylformamide → HCID 58177313, compound

Participants

Reaction Conditions

Reaction Steps

A solution of {5-[7-Iodo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-2-methanesulfonyl-pyrimidin-4-yl}-((S)-1-methanesulfonyl-piperidin-3-yl)-amine (65 mg, 0.091 mmol) and dicyanozinc (11 mg, 0.092 mmol) was combined with dimethylformamide (0.5 ml) (1% water) and the solution thoroughly degassed. To this was added 1,1′-bis(diphenylphosphino)ferrocene (dppf) (1.0 mg, 1.84 μmol) and Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (4.2 mg, 4.6 μmol) and the mixture was heated to 120° C. for 1.5 hours. This was cooled, diluted with brine and water, extracted with ethyl acetate, dried and purified by flash chromatography (silica gel, 0% to 50% ethyl acetate/dichloromethane) to give 2-[2-methanesulfonyl-4-((S)-1-methanesulfonyl-piperidin-3-ylamino)-pyrimidin-5-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonitrile (35 mg, 63%). MS: (ES+): 607.

Provenance & Evidence