Dimethylformamide → HCID 71115094, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[5-(5-bromo-3-methyl-pyridin-2-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester (26 mg), zinc cyanide (7.3 mg), and 1,1′-bis(diphenylphosphino)-ferrocene (3.2 mg) in N,N-dimethylformamide (0.5 mL) is sparged with argon for 5 min. Tris(dibenzylideneacetone)dipalladium (2.6 mg) is added and the resulting mixture is stirred at 120° C. for 3 h. After cooling to room temperature, dichloromethane is added and the mixture is extracted with aqueous K2CO3 solution (10%). The organic phase is washed with brine, dried (MgSO4), and the solvent is evaporated. The residue is chromatographed on silica gel (dichloromethane/methanol 95:5) to give the title compound. Yield: 12 mg (52% of theory); LC (method 2): tR=1.49 min; Mass spectrum (ESI+): m/z=406 [M+H]+.

Provenance & Evidence