1,1'-Carbonyldiimidazole → HCID 178523247, compound

Participants

Reaction Steps

Carbonyldiimidazole (180 mg, 1.11 mmol) was added to a solution of 5-chloro-3-phenylsulfonylindole-2-carboxylic acid (Example 27, Step A) (336 mg, 0.5 mmol) cooled in an ice bath under an inert atmosphere. After 0.5 hours, histamine (125 mg, 1.12 mmol) was added to the yellow solution. After 5 hours the reaction was diluted with water and the product extracted into ethyl acetate. This organic layer was washed with dilute aq. NaHCO3, dried (Na2SO4), filtered through charcoal and the solvents evaporated. Trituration of this residue with methylene chloride gave the crude product. Crystallization from hot ethyl acetate gave analytically pure product, mp 220°-221.5° C.

Provenance & Evidence