Ammonium Chloride → (5-fluoro-2-nitrophenyl)-(1-methyl-1H-pyrazol-4-yl)amine

HRID 243189ノート

反応式

HRID 243189 の反応式
CC(C)([O-])C.[K+].[CH3:7][N:8]1[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]1.F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].[Cl-].[NH4+]>C1COCC1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([NH:13][C:11]2[CH:10]=[N:9][N:8]([CH3:7])[CH:12]=2)[CH:20]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 679672,4-DifluoronitrobenzeneHCID 47709901-methyl-1H-pyrazol-4-amineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 62376936(5-fluoro-2-nitrophenyl)-(1-methyl-1H-pyrazol-4-yl)amine収率 16%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Potassium tert-butoxide (1.16 g, 10.3 mmol) was added to a solution of 1-methyl-1H-pyrazol-4-ylamine (0.50 g, 5.15 mmol) in THF (10 mL) at 0° C. under nitrogen and resultant mixture stirred for 15 min. 2,4-difluoro-1-nitrobenzene (0.98 g, 6.18 mmol) in THF (5 mL) was added and stirring continued for 1 h. The reaction mixture was poured into saturated aqueous ammonium chloride solution and extracted with EtOAc (×3). The combined EtOAc extracts were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by chromatography (SiO2, 0-2% methanol in DCM) to give the title compound as a red gummy solid (0.19 g, 16%). LCMS (Method B): RT 3.12 min [M+H]+ 236.9

後処理

  1. stirringstirring
  2. waitcontinued for 1 h
  3. extractionextracted with EtOAc (×3)
  4. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by chromatography (SiO2, 0-2% methanol in DCM)

出典と根拠

ORDレコード
ord-a753bb206aae44a9b70c3e1dafdc6ef9
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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