Water → 4-cyano-3-(4-cyclopentyl-phenyl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Add cyclopentylzinc bromide (0.5M, 7.2 mL, 3.6 mmol) to 3-(4-bromo-phenyl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.50 g, 1.80 mmol, prepared in example E-3a or E-3b), tris(dibenzylideneacetone)palladium(0) (0.06 g, 0.07 mmol), and triphenylphosphine (0.07 g, 0.27 mmol) in dioxane and heat to 80° C. with stirring. After 18 hours, cool the reaction mixture, and pour into water. Extract the quenched reaction mixture with ethyl acetate. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexane to provide the title compound. Mass spectrum (m/e): 323.3 (M+1).

Provenance & Evidence