Imidazole → HCID 22144737, compound

Participants

Reaction Steps

A mixture of 0.12 gm (0.52 mmol) 5-hydroxymethyl-7-bromobenzofuran 0.070 gm (1.03 mMol) imidazole, and 0.078 gm (0.52 mMol), 0.070 gm (1.03 mMol) imidazole, and 0.078 gm (0.52 mMol) tert-butyldimethylsilyl chloride in 1 mL dimethylformamide was stirred at room temperature for 18 hours. The reaction mixture was diluted with hexane and washed well with water. The remaining organics were dried over magnesium sulfate and concentrated under reduced pressure to provide 0.41 gm (82%) of 5-tert-butyldimethylsilyloxymethyl-7-bromobenzofuran. This material was reacted essentially as described in EXAMPLE 1 to provide 0.085 gm (24%) 1-(5-tert-butyldimethylsilyloxy-methylbenzofur-7-yl)-2-aminopropane. This material was treated with tetrabutylammonium fluoride in tetrahydrofuran for 1 hour at room temperature. The reaction mixture was partitioned between ethyl acetate and water. The phases were separated and the organic phase washed well with water. The remaining organics were concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with dichloromethane containing 2% methanol saturated with ammonia. Fractions containing product were combined and concentrated under reduced pressure to provide 0.028 gm (50%) of 1-(5-hydroxymethylbenzofur-7-yl)-2-aminopropane. The title compound was prepared by reacting this amine with hydrochloric acid.

Provenance & Evidence