Triethylamine → 2-(4-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)PYRAZOLO[1,5-A]PYRIDINE

HRID 354246노트

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HRID 354246 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:20]O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(N(CC)CC)C>COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]3[N:20]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 73025893HCID 73025893, 화합물

생성물 1

HCID 99217692-(4-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)PYRAZOLO[1,5-A]PYRIDINE수율 84%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

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온도
35 °C

실험 절차

To a suspension of 1-(4-fluorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone oxime (189 g, 630 mmol) in DME (700 ml) at −3° C. was added methanesulfonyl chloride (50.5 ml, 650 mmol) and the mixture stirred for 15 minutes. Triethylamine (182 ml, 1.31 mol) in DME (74 ml) was then added dropwise over 15 min. After the addition was complete, the reaction was then warmed to 35° C. for 45 minutes. It was then cooled and filtered, washing with DME (180 ml). To the filtrate was added iron (II) chloride (0.87 g) and the mixture was then heated to 75° C. for 2.5 hour then allowed to cool. Water (700 ml) was added, the resulting solid removed by filtration, washed with water and dried. This solid was dissolved in dichloromethane (1.5 l) and purified in two portions by Biotage chromatography eluting with hexane-ethyl acetate (3:1). Combination and concentration of the appropriate fractions gave 148.3 g (84%) of the title compound.

후처리

  1. additionAfter the addition
  2. temperatureIt was then cooled
  3. filtrationfiltered
  4. washwashing with DME (180 ml)
  5. additionTo the filtrate was added iron (II) chloride (0.87 g)
  6. temperaturethe mixture was then heated to 75° C. for 2.5 hour
  7. temperatureto cool
  8. additionWater (700 ml) was added
  9. customthe resulting solid removed by filtration
  10. washwashed with water
  11. customdried
  12. dissolutionThis solid was dissolved in dichloromethane (1.5 l)
  13. custompurified in two portions by Biotage chromatography
  14. washeluting with hexane-ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-9fe9616c21354b37b615e45b5b963f5d
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756498B2

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