4-(1-Pyrrolidinyl)piperidine → HCID 25190072, compound

Participants

Reaction Steps

In analogy to the procedures described in example 1, intermediate 11 E and in example 47, the title compound has been prepared by the following reaction sequence: i) 5-methyl-3-trifluoromethanesulfonyloxy-3′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (intermediate 11 C) was reacted with pyridine-3-yl-boronic acid in DMF at 80° C. in the presence of potassium phosphate solution and tetrakis-(triphenylphosphine)-palladium to give 5-methyl-3-pyridin-3-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester; ii) saponification of 5-methyl-3-pyridin-3-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester gave 5-methyl-3-pyridin-3-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid; iii) transformation of 5-methyl-3-pyridin-3-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid into its acid chloride and reaction with 4-pyrrolidin-1-yl-piperidine gave the title compound as off-white amorphous solid. MS: 494.3 (MH+).

Provenance & Evidence