HCID 57516647, compound → HCID 67385987, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottomed flask 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide (150 mg, 0.26 mmol) and 1-cyclopropylmethyl-4-tributylstannanyl-1H-imidazole (160 mg, 0.39 mmol) were dissolved in DMF (2 mL). Pd(PPh3)4 (15 mg, 0.013 mmol) and CuI (10 mg, 0.052 mmol) were added. The reaction mixture was heated at 80° C. for 1 h then cooled to room temperature, quenched with H2O and extracted with EtOAc. The organic extracts were washed with saturated aqueous LiCl and brine, dried over MgSO4, and concentrated. The residue was purified by SiO2 chromatography (0-5% MeOH/EtOAc) to afford 162 mg (99%) of 2-(1-cyclopropylmethyl-1H-imidazol-4-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide as a viscous colorless oil.

Provenance & Evidence