Methyl iodide → ethyl 1-(3-fluorophenyl)-5-(N-methylacetamido)-1H-pyrazole-4-carboxylate

HRID 659706노트

반응식

HRID 659706 반응식
[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[N:8]=[CH:7][C:6]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:3])[CH3:2].[H-].[Na+].[CH3:24]I.[Cl-].[NH4+]>CN(C=O)C.C1COCC1>[F:16][C:12]1[CH:11]=[C:10]([N:9]2[C:5]([N:4]([CH3:24])[C:1](=[O:3])[CH3:2])=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[N:8]2)[CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57708075ethyl 5-acetamido-1-(3-fluorophenyl)-1H-pyrazole-4-carboxylate

생성물 1

HCID 57708074ethyl 1-(3-fluorophenyl)-5-(N-methylacetamido)-1H-pyrazole-4-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethyl 5-acetamido-1-(3-fluorophenyl)-1H-pyrazole-4-carboxylate (3.56 g, 12.2 mmol) in 8 mL of DMF and 8 mL of THF at 0° C. was treated with NaH (60% wt. in mineral oil, 850 mg, 21.2 mmol). After 10 min of stirring, MeI (1.4 mL, 21.9 mmol) was added, and the reaction mixture was stirred at 0° C. for 15 min followed by RT for 1 h. the mixture was treated with saturated ammonium chloride and extracted with EtOAc twice. The combined EtOAc layers were washed with brine, dried and concentrated. Purification of the resulting crude material on an ISCO (80 g column, 30-50% EtOAc in Hexanes) provided ethyl 1-(3-fluorophenyl)-5-(N-methylacetamido)-1H-pyrazole-4-carboxylate as a colorless amorphous solid. MS (ESI, pos.ion) m/z: 306.1 (M+1).

후처리

  1. stirringthe reaction mixture was stirred at 0° C. for 15 min
  2. waitfollowed by RT for 1 h.
  3. extractionextracted with EtOAc twice
  4. washThe combined EtOAc layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customPurification of the resulting crude material on an ISCO (80 g column, 30-50% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-6486a3bc76f74066b8f9dee78148bf74
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080546B2

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