HCID 22144789, compound → HCID 22144785, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.20 gm (0.54 mMol) N-tert-butoxycarbonyl 1-(3-bromo-5-fluorobenzofur-7-yl)-2-aminopropane, 0.95 gm (5 mMol) copper(I) iodide, and 0.43 gm (4.78 mMol) copper(I) cyanide in 10 mL dimethylformamide was purged with nitrogen for 15 minutes. The mixture was then heated at 120° C. An additional equivalent of copper(I) iodide and copper(I) cyanide were added and the reaction continued at 120° C. for about 16 hours. After cooling to room temperature the reaction mixture was diluted with dichloromethane and then silica gel was added. The solvents were removed under reduced pressure and the dry silica gel remaining was loaded on the top of a silica gel column. The column was then eluted with a gradient of hexane containing from 17% to 20% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.010 gm (6%) of the desired compound.

Provenance & Evidence