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Water → 2-(3,5-Dichlorophenyl)-6-Trifluoromethylpyrazolo[1,5-a]Pyridine

HRID 354255
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HRID 354255 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[N:21]O)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.C(N(CC)CC)C.O>COCCOC.[Fe](Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]3[N:21]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 740579941-(3,5-Dichlorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone oxime

생성물 1

HCID 235133492-(3,5-Dichlorophenyl)-6-Trifluoromethylpyrazolo[1,5-a]Pyridine수율 25.4%

시약·촉매·용매 2

HCID 24458
Ferrous Chloride
촉매
HCID 80711,2-Dimethoxyethane용매

실험 절차

To a suspension of 1-(3,5-dichlorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone oxime (13.30 g, 38 mmol) in DME (52 ml) at 5° C. was added TFAA (6.25 ml, 44 mmol) and the mixture stirred for 10 minutes. Triethylamine (18.6 ml, 134 mmol) was then added dropwise over 15 min. After the addition was complete, the reaction mixture was then warmed to room temperature. After stirring for 1 hour, iron (II) chloride (56 mg) was added and the mixture was then heated to 75° C. for 1 hour then allowed to cool. The mixture was poured into water (500 ml) and extracted with dichloromethane (300 ml). The organic extracts were dried over MgSO4 and concentrated under reduced pressure to ca. 50 ml. This residue was purified by filtration through a layer of silica gel washing with further dichloromethane. The filtrate was concentrated to dryness to give 3.2 g (25%) of the title compound.

후처리

  1. additionAfter the addition
  2. stirringAfter stirring for 1 hour
  3. temperaturethe mixture was then heated to 75° C. for 1 hour
  4. temperatureto cool
  5. extractionextracted with dichloromethane (300 ml)
  6. dry with materialThe organic extracts were dried over MgSO4
  7. concentrationconcentrated under reduced pressure to ca. 50 ml
  8. filtrationThis residue was purified by filtration through a layer of silica gel washing with further dichloromethane
  9. concentrationThe filtrate was concentrated to dryness

출처 및 근거

ORD 기록
ord-96448e63c28a4714b218cbe42733735c
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06756498B2

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