HCID 59540985, compound → HCID 59540523, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3,4-dimethoxy-phenyl)-7-iodo-5-(toluene-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazine (380 mg, 0.71 mmol), CuCN (256, 2.8 mmol), bis(dibenzylideneacetone)palladium(0) [Pd2(dba)3] (26 mg, 0.03 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (63 mg, 0.11 mmol) in dioxane (7 mL) was stirred at 90° C. overnight. Additional CuCN (50, 0.56 mmol), Pd2(dba)3 (6 mg, 0.01 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (15 mg, 0.03 mmol) was added to the reaction mixture which was then stirred at 90° C. for 4 h and partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic phases were concentrated. The residue was purified by flash chromatography using 40 g of silica gel and 0-70% EtOAc in hexanes as eluant to afford 60 mg (20%) of 2-(3,4-dimethoxy-phenyl)-5-(toluene-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonitrile as a white solid and 50 mg (16%) as a yellow solid. MP 233-234° C., M+H 435.

Provenance & Evidence