تفاعل #41699

معادلة التفاعل

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

المذيبات

tetrahydrofuran

Water

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر