Ethanol → HCID 86669278, compound

Participants

Reaction Steps

A flask was charged with 1-methylethyl (1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation see Example 61) (100 mg, 0.271 mmol), potassium carbonate (74.9 mg, 0.542 mmol), 1,3,5-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (77 mg, 0.325 mmol) and tetrakis(triphenylphosphine)palladium(0) (15.65 mg, 0.014 mmol) then filled with ethanol (1 mL) and toluene (1 mL) and the resulting mixture was refluxed under nitrogen for 18 h then cooled to room temperature and partitioned between water (40 mL) and EtOAc (40 mL). The layers were separated and the aqueous phase was extracted with EtOAc (40 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 50% AcOEt in Hexanes) gave 1-methylethyl[(cis)-1-acetyl-2-methyl-6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (33 mg, 0.078 mmol, 29%) as a dark yellow solid.

Provenance & Evidence