Ethanol → HCID 68185444, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Example 4) (200 mg, 0.542 mmol), potassium carbonate (150 mg, 1.083 mmol), tetrakis(triphenylphosphine)palladium(0) (6.26 mg, 5.42 μmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (149 mg, 0.650 mmol) then filled with ethanol (2 mL) and toluene (2 mL) and the resulting mixture was stirred under nitrogen at 90° C. for 16 h then cooled to room temperature and partitioned between water (20 mL) and EtOAc (60 mL). The layers were separated and the aqueous phase was extracted with EtOAc (30 mL). The combined organic phases were washed with brine (30 mL), dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 10 to 55% AcOEt in hexanes) gave 1-methylethyl[(2S,4R)-1-acetyl-6-(4-cyanophenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (176 mg, 0.45 mmol, 83%) as a white solid. LCMS (method G): Retention time 1.03 min, [M+H]+=392.0

Provenance & Evidence