Реакция #41699

Уравнение реакции

n-butyllithium

hexane

(3R)-3-(tert-butyl(dimethyl)silyl)oxy-1-butyne

N-(3-fluoro-4-((N-methoxy-N-methylamino)carbonyl)phenyl)pyrazine-2-carboxamide

→

compound

N-(4-((4R)-4-((tert-butyl(dimethyl)silyl)oxy)-2-pentynoyl)-3-fluorophenyl)pyrazine-2-carboxamide

Растворители

tetrahydrofuran

Water

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe reaction liquid
2. 2
   Другоеthe reaction liquid
3. 3
   workup.STIRRINGstirred for 2 hours
4. 4
   Экстракцияextracted with ethyl acetate
5. 5
   Сушкаdried with anhydrous magnesium sulfate
6. 6
   ДругоеThe solvent was evaporated away under reduced pressure
7. 7
   Другоеthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 1/1)

Методика

10.8 ml of n-butyllithium (2.46 M hexane solution was added to a tetrahydrofuran (80 ml) solution of 4.92 g of (3R)-3-(tert-butyl(dimethyl)silyl)oxy-1-butyne at −78° C., and the reaction liquid was stirred at the same temperature for 1 hour. A tetrahydrofuran (60 ml) solution of 2.7 g of N-(3-fluoro-4-((N-methoxy-N-methylamino)carbonyl)phenyl)pyrazine-2-carboxamide was added to it at −78° C., and the reaction liquid was heated up to room temperature and stirred for 2 hours. Water was added to the reaction liquid, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 1/1) to obtain the entitled compound as a yellow solid.

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