Reacción #68396

Ecuación de reacción

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

Disolventes

CH3CN

Et3N

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas purged with N2 for 10 min
2. 2
   Otrothe mixture was purged with N2 for another 5 min
3. 3
   Otrothe reaction was quenched with aqueous NaHCO3
4. 4
   Extracciónextracted with EtOAc (×3)
5. 5
   LavadoThe combined organic layer was washed with brine
6. 6
   Secadodried over Na2SO4
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)

Procedimiento

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.

Fuente