Dichloromethane → 1-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

HRID 971133노트

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HRID 971133 반응식
[F:1][C:2]([F:16])([F:15])[C:3](Br)=[N:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.CC[N:19]([CH2:22][CH3:23])CC.[CH2:24](Cl)Cl.CCO[C:30]([CH3:32])=[O:31]>C1(C)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]2[C:32]3[C:30](=[O:31])[NH:19][CH2:22][CH2:23][C:24]=3[C:3]([C:2]([F:16])([F:15])[F:1])=[N:4]2)=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8857Ethyl Acetate2회HCID 713581942,2,2-Trifluoro-N-(4-methoxyphenyl)ethanehydrazonoyl bromide

생성물 1

HCID 218914731-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one수율 39%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
85 °C

실험 절차

Part B. The product from Part A (5.50 g, 41.98 mmol) and 2,2,2-trifluoro-N-(4-methoxyphenyl)-ethanehydrazonoyl bromide (12.90 g, 43.58 mmol) were stirred in toluene (100 mL) at room temperature under N2. Et3N (28.0 mL, 200.1 mmol) was then added. The mixture was stirred at 85° C. for 15 h. It was cooled to room temperature and extracted with EtOAc (3×). The organic layers were washed with H2O (2×) and brine (2×), dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, CH2Cl2, then CH2Cl2:EtOAc=4:1, then EtOAc) to produce 1-(4-methoxyphenyl)-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one as a light-tan solid (5.09 g, yield: 39%). LC/MS (ESI+) 312.4 (M+H)+.

후처리

  1. temperatureIt was cooled to room temperature
  2. extractionextracted with EtOAc (3×)
  3. washThe organic layers were washed with H2O (2×) and brine (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by flash column chromatography (silica gel, CH2Cl2

출처 및 근거

ORD 기록
ord-6570251ad94b48ee9ff90b10fa503698
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312214B2

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