Sodium Carbonate → HCID 71208354, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-(5-bromo-2,3-dihydro-benzofuran-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.00 g) and 4-(methoxycarbonyl)phenyl boronic acid (565 mg) in N,N-dimethylformamide (50 mL) a 2 M aqueous Na2CO3 solution (3.27 mL) is added. The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene].CH2Cl2 complex (213 mg) is added. The resulting mixture is stirred for 5 h at 90° C. After cooling to room temperature water (50 mL) and ethyl acetate (100 mL) are added and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water and brine, dried over MgSO4, and the solvent is evaporated. The residue is mixed with trifluoroacetic acid (1.4 mL), dichloromethane (1.4 mL), and water (0.15 mL) and stirred for 3 h. The solvents are evaporated and the residue is mixed with diethyl ether. The title compound is collected by filtration as the trifluoroacetic acid salt. LC (method 8): tR=1.19 min; Mass spectrum (ESI+): m/z=338 [M+H]+.

Provenance & Evidence