تفاعل #158328

معادلة التفاعل

ammonium chloride

ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

sodium hydride

N-fluoro-N′-chloromethyltriethylenediamine bis(tetrafluoroborate)

→

title compound

المردود 60.6%

ethyl 8-fluoro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

المردود 60.6%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   درجة الحرارةcooling
3. 3
   درجة الحرارةcooling
4. 4
   workup.STIRRINGthe mixture was stirred for 30 min under ice-
5. 5
   درجة الحرارةcooling
6. 6
   استخلاصthe mixture was extracted with ethyl acetate
7. 7
   غسيلThe extract was washed with saturated brine
8. 8
   تجفيفdried over anhydrous sodium sulfate
9. 9
   أخرىthe solvent was evaporated under reduced pressure
10. 10
    أخرىThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

الإجراء التجريبي

Under an argon atmosphere, ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (200 mg) was added to a suspension of sodium hydride (60%, 23 mg) in DMF (2 mL) under ice-cooling. The reaction mixture was stirred for 30 min under ice-cooling, N-fluoro-N′-chloromethyltriethylenediamine bis(tetrafluoroborate) (371 mg) was added under ice-cooling, and the mixture was stirred for 30 min under ice-cooling. The reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (127 mg).

المصدر