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0 °C

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.

1. customwas purged with N2 for 10 min
2. customthe mixture was purged with N2 for another 5 min
3. customthe reaction was quenched with aqueous NaHCO3
4. extractionextracted with EtOAc (×3)
5. washThe combined organic layer was washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customThe residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)