Réaction #41699

Équation de réaction

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

Solvants

tetrahydrofuran

Water

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source