Butyl iodide → Methyl 1-butyl-1H-indazole-6-carboxylate

HRID 14164

반응식

HRID 14164 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].I[CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C>[CH2:17]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[N:2]1)[CH2:18][CH2:19][CH3:20]

참가 물질

5

반응물 3

HCID 10962Butyl iodide2회HCID 24758Sodium hydrideHCID 286535methyl 1H-indazole-6-carboxylate

생성물 1

HCID 21086132Methyl 1-butyl-1H-indazole-6-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a mixture of methyl 1H-indazole-6-carboxylate (0.95 g) in DMF (10 mL) was added 60% NaH (0.216 g). The mixture was heated to 60° C. and 1-iodobutane (0.61 mL) was added. The mixture was heated at 60° C. for 72 h and 1-iodobutane (0.61 mL) was added every 24 h. The mixture was removed from heat and cooled to room temperature and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed three times with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 5% ethyl acetate in hexanes as eluent to give 0.356 g of the title compound: 1H NMR (CDCl3) δ 0.938, 1.34, 1.92, 3.97, 4.43, 7.73, 7.79, 8.03, 8.18.

후처리

  1. temperatureThe mixture was heated at 60° C. for 72 h
  2. customThe mixture was removed
  3. temperaturefrom heat
  4. temperaturecooled to room temperature
  5. custompartitioned between water and ethyl acetate
  6. customThe layers were separated
  7. washthe organic layer washed three times with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2d9bf91054c84e92bc1e3402ab66d8ca
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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