Potassium Carbonate → HCID 52934566, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see example 4) (78.6 mg, 0.213 mmol), phenyl boronic acid (31.1 mg, 0.255 mmol), potassium carbonate (73.5 mg, 0.532 mmol) and tetrakis(triphenylphosphine)palladium(0) (12.30 mg, 10.64 μmol) in ethanol (2.5 mL) and toluene (2.5 mL) was degassed under house vacuum and quenched several times with nitrogen, and then was heated at 100° C. for 30 min before being cooled to room temperature. The mixture was filtered through celite and the insoluble washed with EtOH. Most of the solvent was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 25 to 55% AcOEt in hexanes) gave 1-methylethyl [(2S,4R)-1-acetyl-2-methyl-6-phenyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (71.6 mg, 0.195 mmol, 92%) as a white solid.

Provenance & Evidence