Methyl iodide → Methyl-4-(5-iodoindazole-1-yl)-benzoate

HRID 13139

反応式

HRID 13139 の反応式
[C:1]([O-])([O-])=O.[K+].[K+].[I:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)[N:12]=[CH:11]2.CI>CN(C=O)C>[CH3:1][O:22][C:21](=[O:23])[C:20]1[CH:19]=[CH:18][C:17]([N:13]2[C:14]3[C:10](=[CH:9][C:8]([I:7])=[CH:16][CH:15]=3)[CH:11]=[N:12]2)=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 593397454-(5-Iodoindazole-1-yl)-benzoic acid

生成物 1

HCID 66812731Methyl-4-(5-iodoindazole-1-yl)-benzoate収率 76.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

K2CO3 (7.35 g, 53.2 mmol) is suspended in 110 mL DMF. 4-(5-iodoindazole-1-yl)-benzoic acid (17.6 g, 48.33 mmol), dissolved in 25 mL DMF, is added dropwise. The reaction mixture is stirred for 30 min at r.t. Subsequently CH3I (3.31 mL, 53.2 mmol) is added dropwise (temperature rises to 30° C.). The reaction mixture is stirred overnight at r.t. and then poured on ice water. It is three times extracted with ethyl acetate. The combined organic extracts are washed twice with water and brine. After drying over Na2SO4 and filtration the solvent is evaporated. The residue is purified by chromatography (silicagel, eluents: ethyl acetate/hexane) yielding 14.03 g (76.8%) of the title compound.

後処理

  1. additionis added dropwise
  2. stirringThe reaction mixture is stirred overnight at r.t.
  3. additionpoured on ice water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts are washed twice with water and brine
  6. dry with materialAfter drying over Na2SO4 and filtration the solvent
  7. customis evaporated
  8. customThe residue is purified by chromatography (silicagel, eluents: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-4339b0ab9d0b40d582cb4138a77dda1e
出典データセット
uspto-grants-2010_06
特許番号
US07728030B2

関連ノート

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