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

HRID 13139

반응식

HRID 13139 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4339b0ab9d0b40d582cb4138a77dda1e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728030B2

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