Реакция #68396

Уравнение реакции

2-butyramido-4-nitrophenyl trifluoromethanesulfonate

Compound 118

2-butyramido-4-nitrophenyl trifluoromethanesulfonate

3-methyl-1-butyne

→

title compound

N-(2-(3-Methylbut-1-ynyl)-5-nitrophenyl)butyramide

Растворители

CH3CN

Et3N

Условия реакции

Обработка

1. 1
   Другоеwas purged with N2 for 10 min
2. 2
   Другоеthe mixture was purged with N2 for another 5 min
3. 3
   Другоеthe reaction was quenched with aqueous NaHCO3
4. 4
   Экстракцияextracted with EtOAc (×3)
5. 5
   ПромывкаThe combined organic layer was washed with brine
6. 6
   Сушкаdried over Na2SO4
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеThe residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)

Методика

A mixture of 2-butyramido-4-nitrophenyl trifluoromethanesulfonate (Compound 118, 200 mg, 0.56 mmol), CuI (32 mg, 0.17 mmol), and n-Bu4NI (311 mg, 0.84 mmol) in CH3CN (5 ml) and Et3N (1 ml) was purged with N2 for 10 min and Pd(PPh3)4 (64 mg, 0.056 mmol) was added and the mixture was purged with N2 for another 5 min. The mixture was then cooled to 0° C. and 3-methyl-1-butyne (76 mg, 1.12 mmol) was added. After 5 min, the reaction was quenched with aqueous NaHCO3, extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes) to yield the title compound.

Источник