反应详情

温度

120 °C

A flask was charged with ethyl (4-bromophenyl)acetate (0.174 mL, 1.000 mmol), 1-methylethyl[(2S,4R)-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 52) (416 mg, 1 mmol), potassium carbonate (415 mg, 3.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (73.2 mg, 0.100 mmol) then filled with 1,4-dioxane (6 mL) and water (2 mL) and flushed with nitrogen. The resulting mixture was stirred under microwave irradiation at 120° C. for 30 min then cooled to room temperature. Most of the 1,4-dioxane was removed in vacuo and the residue was partitioned between AcOEt and water. The layers were separated and the aqueous phase was extracted with AcOEt. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 on a 25 G silica cartridge (gradient: 5 to 25% of (10% MeOH in DCM) in DCM) gave ethyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetate (270 mg, 0.597 mmol, 59.7% yield).

1. customfor a preparation
2. customflushed with nitrogen
3. temperaturethen cooled to room temperature
4. customMost of the 1,4-dioxane was removed in vacuo
5. customthe residue was partitioned between AcOEt and water
6. customThe layers were separated
7. extractionthe aqueous phase was extracted with AcOEt
8. washThe combined organic phases were washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated in vacuo
11. customPurification of the residue by SP4 on a 25 G silica cartridge (gradient: 5 to 25% of (10% MeOH in DCM) in DCM)