反应详情

温度

100 °C

A mixture of 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) (100 mg, 0.240 mmol), ethyl (4-bromophenyl)acetate (70.1 mg, 0.288 mmol), potassium carbonate (100 mg, 0.721 mmol) and tetrakis(triphenylphosphine)palladium(0) (13.88 mg, 0.012 mmol) was degassed under house vacuum and quenched several times with nitrogen, and then was heated at 100° C. for 1 h before being cooled to room temperature and partitioned between AcOEt (60 mL) and water (30 mL). The layers were separated and the organic phase was washed with brine, dried on MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 5 to 25% AcOEt in hexanes) gave ethyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetate (33.9 mg, 0.075 mmol, 31%) as a colourless solid.

1. customwas degassed under house vacuum
2. customquenched several times with nitrogen
3. temperaturebefore being cooled to room temperature
4. custompartitioned between AcOEt (60 mL) and water (30 mL)
5. customThe layers were separated
6. washthe organic phase was washed with brine
7. customdried on MgSO4
8. concentrationconcentrated in vacuo
9. customPurification of the residue by flash chromatography on silica gel (gradient: 5 to 25% AcOEt in hexanes)