Pyridine → HCID 86611445, compound

Participants

Reaction Conditions

Reaction Steps

Add trifluoromethanesulfonic anhydride (1.2 Eq.) to 4-cyano-3-(4-hydroxy-phenyl)-1,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in example E-238) and pyridine (1.5 Eq) in methylene chloride dropwise with stirring at 0° C. Stir the reaction mixture for 2 hours and then allow the reaction to warm to room temperature. Wash the organic layer with 1.0 N HCl, water, dry over potassium carbonate, filter, and concentrate under reduced vacuum. Purify the residue by silica gel chromatography (Chromatotron™) eluting with methylene chloride to provide the title compound as a yellow solid. Mass spectrum (m/e): 417.1 (M*+1): (Bruker 300) 1H NMR (CDCl3) δ 7.29-7.32 (2H, d), 7.27-7.29 (2H, d), 4.01-4.11 (2H, dd), 3.85-3.89 (3H, s), 2.43-2.47 (3H, s), 0.90-1.00 (3H, t).

Provenance & Evidence