Potassium Carbonate → HCID 52934330, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of palladium(II) acetate (60 mg, 0.267 mmol) and Xantphos (380 mg, 0.797 mmol) in t-butanol (50 mL) and water (100 μL) was heated at 90° C. for 5 min. The hot solution was then added to a mixture of 4-methylimidazole (530 mg, 6.46 mmol), 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Example 4) (2.0 g, 5.4 mmol) and potassium carbonate (1.12 g, 8.1 mmol). The resulting mixture was refluxed for 24 h then cooled to room temperature and the insoluble were filtered off. Most of the solvents were removed in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 6% MeOH in DCM) gave 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (189 mg, 0.51 mmol, 9%)

Provenance & Evidence