Hydrochloric Acid → 1-Methylethyl {(cis)-1-acetyl-6-[6-(dimethylamino)-3-pyridinyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride

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Reaction Conditions

Reaction Steps

In a carousel tube, 1-methylethyl[(cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Example 61) (80 mg, 0.217 mmol), potassium carbonate (59.9 mg, 0.433 mmol), tetrakis(triphenylphosphine)palladium(0) (12.52 mg, 10.83 μmol) and [6-(dimethylamino)-3-pyridinyl]boronic acid hydrate (47.8 mg, 0.26 mmol, available from Apollo) were dissolved in Ethanol (0.5 mL) and Toluene (0.5 mL). The tube was placed in a carousel and heated under nitrogen for 18 hr at 90° C. The reaction mixture was filtered and the solvent evaporated before being taken up in DCM and purified by SP4 on a 12+M silica cartridge using a gradient of 20-100% EtOAc in cyclohexane. Appropriate fractions were collected and concentrated. The sample was dissolved in 1:1 MeOH:DMSO 1 mL and purified by MDAP. The solvent was evaporated in vacuo. To form a salt, the product was dissolved in MeOH and HCl (0.217 mL, 0.217 mmol) 1M in ether was added. Solvent was evaporated to yield the product as a pale yellow solid (76 mg). LCMS (Method C): Rt=0.66, MH+=411

Provenance & Evidence