Butyl iodide → Methyl 1-butyl-4-iodo-1H-indole-6-carboxylate

HRID 348968

반응식

HRID 348968 반응식
[I:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[K+].I[CH2:18][CH2:19][CH2:20][CH3:21]>CN(C=O)C>[CH2:18]([N:6]1[C:7]2[C:3](=[C:2]([I:1])[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=2)[CH:4]=[CH:5]1)[CH2:19][CH2:20][CH3:21]

참가 물질

5

반응물 3

HCID 10962Butyl iodideHCID 14797Potassium HydroxideHCID 851585methyl 4-iodo-1H-indole-6-carboxylate

생성물 1

HCID 21086136Methyl 1-butyl-4-iodo-1H-indole-6-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a mixture of methyl 4-iodo-1H-indole-6-carboxylate (1.0 g) in DMF (10 mL) was added potassium hydroxide (0.392 g) and 1-iodobutane (0.8 mL). The mixture was heated to 80° C. for 18 h. The mixture was cooled to room temperature and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 20% ethyl acetate in hexanes as eluent to give 0.73 g of the title compound: 1H NMR (CDCl3) δ 0.940, 1.32, 1.81, 3.95, 4.15, 6.45, 7.31, 8.09, 8.18.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer washed twice with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b85ba07897364fb493119f93cc386d1a
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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