Aniline → HCID 57831046, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.206 g, 0.50 mmol), potassium carbonate (0.152 g, 1.10 mmol), copper (I) iodide (0.014 g, 0.075 mmol), proline (0.017 g, 0.15 mmol) and aniline (0.46 mL, 5 mmol) in 1 mL of dimethylsulfoxide was stirred at 90° C. for 5 d, then allowed to cool. The mixture was partitioned between 50 mL of ethyl acetate and 30 mL of water, and the organic layer was washed with 30 mL of a sat. aq. NaCl solution, dried over MgSO4, and concentrated to a residue. Column chromatography (0→45% EtOAc/hexanes) afforded 0.102 g (48%) of 2,2-dimethyl-1-[2-phenylamino-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one as a pale orange solid.

Provenance & Evidence