反应详情

温度

100 °C

A flask was charged with 2-[3,4-bis(methyloxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.429 g, 1.625 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) (0.5 g, 1.354 mmol), a saturated NaHCO3 aqueous solution (1.5 mL, 1.354 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II)-DCM adduct (0.111 g, 0.135 mmol) then filled with 1,4-dioxane (7 mL). The resulting mixture was degassed by bubbling nitrogen in to it, stirred at 100° C. for 1 hr under microwave irradiation then cooled to room temperature. The reaction mixture was filtered through celite and concentrated in vacuo. The residue was partitioned between EtOAC (30 mL) and water (30 mL) and the layers were separated. The organic phase was washed with brine (25 mL) dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 60% AcOEt in hexanes) gave 1-methylethyl {(2S,4R)-1-acetyl-6-[3,4-bis(methyloxy)phenyl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (327 mg, 0.766 mmol, 56.6%). LCMS (method A): Retention time 1.02 min, [M+H]+=427.18

1. customThe resulting mixture was degassed
2. customby bubbling nitrogen in to it
3. temperaturethen cooled to room temperature
4. filtrationThe reaction mixture was filtered through celite and
5. concentrationconcentrated in vacuo
6. customThe residue was partitioned between EtOAC (30 mL) and water (30 mL)
7. customthe layers were separated
8. washThe organic phase was washed with brine (25 mL)
9. dry with materialdried over MgSO4
10. concentrationconcentrated in vacuo
11. customPurification of the residue by flash chromatography on silica gel (gradient: 0 to 60% AcOEt in hexanes)