1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-[5-(4-Methanesulfonyl-piperazin-1-yl)-2-methyl-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

4-(5-Chloro-2-methyl-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg) is added to a mixture of 1-(methylsulfonyl)piperazine hydrochloride (70 mg), Pd2(dba)3 (65 mg), Xantphos (123 mg), and potassium tert-butylate (75 mg) in toluene (4 mL) under an argon atmosphere. The reaction mixture is stirred in an oil bath at 105° C. over night. After cooling to room temperature water is added and the mixture is extracted with ethyl acetate. The combined extracts are concentrated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100) to give the title compound. LC (method 1): tR=1.03 min; Mass spectrum (ESI+): m/z=481 [M+H]+.

Provenance & Evidence