HCID 57516653, compound → HCID 86657875, compound

Participants

Reaction Conditions

Reaction Steps

A pressure tube was charged with 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (0.110 g, 0.31 mmol), Pd(PPh3)4 (0.020 g, 0.017 mmol), CuI (0.012 g, 0.063 mmol) and the above-prepared crude 1-(2,5-difluorophenyl)-4-(tributylstannyl)-1H-imidazole (0.198 g) in 3 mL of DMF. The tube was capped under Ar and the orange yellow mixture stirred at 80° C. for 1.5 h, then allowed to cool. The mixture was partitioned between 20 mL of ethyl acetate and 20 mL of water+20 mL of a sat. aq. NH4Cl solution. The organic layer was washed with 20 mL of a sat. aq. NaCl solution, dried over Na2SO4, filtered and concentrated. Column chromatography (20-100% EtOAc/hexanes) of the residue afforded 0.087 g (62%) of 2-[1-(2,5-difluoro-phenyl)-1H-imidazol-4-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as a slightly impure yellow oil, which was used without further purification. MS: (M+Na)+=478.

Provenance & Evidence