Potassium Carbonate → HCID 86669228, compound

Participants

Reaction Conditions

Reaction Steps

1-methylethyl[(cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Example 61) (1.6 g, 4.33 mmol), potassium carbonate (1.198 g, 8.67 mmol), tetrakis(triphenylphosphine)palladium(0) (0.250 g, 0.217 mmol) and (4-formylphenyl)boronic acid (0.780 g, 5.20 mmol) were dissolved in Ethanol (10 mL) and Toluene (10 mL). The reaction mixture was degassed for 30 min then stirred and heated under nitrogen for 1 hr at 100° C. The reaction mixture was filtered and the solvent evaporated under vacuum. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was dried through a hydrophobic frit and concentrated in vacuo. The residue was dissolved with dichloromethane and purified by SP4 on a 40+M silica cartridge using a gradient 20-75% ethyl acetate in cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the required product (1.4 g) as a yellow solid. LCMS (Method B): Rt 0.99, MH+=395

Provenance & Evidence