N,N'-Dimethylethylenediamine → 3-{4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-phenylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Combine 3-carbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.21 g, 0.96 mmol), 6-(4-bromo-phenyl)-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (0.2 g, 0.48 mmol), Cs2CO3 (0.31 g, 0.96 mmol), 1,4-dioxane (5 mL), and CuI (0.037 g, 0.19 mmol). Purge the mixture with nitrogen for 10 min and then add sym-dimethylethylene diamine (0.034 g, 0.38 mmol). Heat the mixture at 100° C. overnight. Cool the mixture to RT, dilute with CH2Cl2, and wash twice with a solution of 5% NH4OH/H2O. Dry the organic layer over Na2SO4, filter, and concentrate. Filter the crude with Et2O and water to give 0.117 g (43%) of the title compound. LC-ES/MS m/z (35Cl) 494.0 [M−tert Bu+H]+.

Provenance & Evidence