反応 #41699

反応方程式

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

溶媒

tetrahydrofuran

Water

tetrahydrofuran

反応条件

後処理

1. 1
   その他the reaction liquid
2. 2
   その他the reaction liquid
3. 3
   workup.STIRRINGstirred for 2 hours
4. 4
   抽出extracted with ethyl acetate
5. 5
   乾燥dried with anhydrous magnesium sulfate
6. 6
   その他The solvent was evaporated away under reduced pressure
7. 7
   その他the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 1/1)

実験手順

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.

出典