Potassium Carbonate → HCID 52934330, compound

Participants

Reaction Conditions

Reaction Steps

A stock solution of tert-butanol (5 mL) and water (10 μl) was prepared and degassed under house vacuum and quenched several times with nitrogen. A mixture of palladium(II) acetate (6 mg, 5 mmol) and Xantphos (38 mg, 0.081 mmol) in the stock solvent (4 mL) was heated at 80° C. for 1 min under microwave irradiation then cooled to room temperature. The solution was then added to a mixture of 4-methylimidazole (53 mg, 0.65 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) (200 mg, 0.54 mmol) and potassium carbonate (112 mg, 0.81 mmol). The resulting mixture was stirred at 110° C. for 15 h under microwave irradiation 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 (3 mg, 0.0081 mmol, 1.5%)

Provenance & Evidence