反应详情

温度

90 °C

In a carousel tube, 1-methylethyl[(cis)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 12) (80 mg, 0.192 mmol), potassium carbonate (53.1 mg, 0.384 mmol), tetrakis(triphenylphosphine)palladium(0) (11.10 mg, 9.61 μmol) and 1,1-dimethylethyl 4-(5-iodo-2-pyrazinyl)-1-piperazinecarboxylate (for a preparation see Intermediate 13) (90 mg, 0.231 mmol) 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 10-60% EtOAc in cyclohexane. Appropriate fractions were collected and concentrated. The samples were dissolved in 1:1 MeOH:DMSO 1 mL and purified by MDAP. The solvent was evaporated in vacuo to give the protected product. The sample was then dissolved in MeOH and acetyl chloride (0.015 mL, 0.211 mmol) was added. The solvent was then evaporated via nitrogen blow down to give the final product (63.9 mg) as an HCl salt. LCMS (Method C): Rt=0.65, MH+=453

1. filtrationThe reaction mixture was filtered
2. customthe solvent evaporated
3. custompurified by SP4 on a 12+M silica cartridge
4. customAppropriate fractions were collected
5. concentrationconcentrated
6. dissolutionThe samples were dissolved in 1:1 MeOH
7. customDMSO 1 mL and purified by MDAP
8. customThe solvent was evaporated in vacuo
9. customto give the protected product
10. customThe solvent was then evaporated via nitrogen