Reaktion #68396

Reaktionsgleichung

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

Lösungsmittel

CH3CN

Et3N

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas purged with N2 for 10 min
2. 2
   Sonstigethe mixture was purged with N2 for another 5 min
3. 3
   Sonstigethe reaction was quenched with aqueous NaHCO3
4. 4
   Extraktionextracted with EtOAc (×3)
5. 5
   WaschenThe combined organic layer was washed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)

Vorschrift

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.

Quelle