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

HRID 659706ノート

反応式

HRID 659706 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6486a3bc76f74066b8f9dee78148bf74
出典データセット
uspto-grants-2011_12
特許番号
US08080546B2

反応ノート

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