Potassium Carbonate → HCID 52934567, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 52) (136. mg, 0.327 mmol), 2-(4-bromophenyl)ethanol (79 mg, 0.392 mmol), potassium carbonate (113 mg, 0.817 mmol) and tetrakis(triphenylphosphine)palladium(0) (18.87 mg, 0.016 mmol) was degassed under house vacuum for 15 min and quenched several times with nitrogen, then was then stirred at 100° C. under nitrogen for 50 min before being cooled to room temperature. Most of the solvent was removed in vacuo and the residue was partitioned between AcOEt (20 mL) and water (15 mL). The layers were separated and the aqueous phase was extracted with AcOEt (15 mL). The combined organic layers were washed with brine (15 mL), dried over MgSO4, concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 50 to 80% AcOEt in Hexanes) gave a residue which was further purified by MDAP (modifier ammonium formate) to give 1-methylethyl {(2S,4R)-1-acetyl-6-[4-(2-hydroxyethyl)phenyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (42 mg, 0.102 mmol, 31%).

Provenance & Evidence