Sodium Carbonate → HCID 45274382, compound

Participants

Reaction Steps

General procedure E was followed using 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (75 mg, 0.27 mmol), 2-thiophene boronic acid (44 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium(0) (16 mg, 0.014 mmol), acetonitrile (3 mL) and 0.5 M sodium carbonate (0.77 mL, 0.38 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 96:4-80:20, biotage 25+S) to yield the a mixture of starting material and product (50 mg, 2:5), along with dehalogenated monochloro starting material (7 mg, 11%). The product/starting material mixture was further purified by preparative hplc (CH3CN, H2O, gradient 1:9 to 9:1, 15 min) to furnish the title compound (9 mg, 10%) as a clear colourless oil, along with recovered 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide (30 mg, 40%) as a white solid, LC-MS (ESI, 4 min) Rt 2.31 min, m/z 322 (100%, [M+H]+); m/z (ESI) C15H16N3OSCl requires 321.0703, found [M+H]+ 321.0700.

Provenance & Evidence