Potassium Iodide → methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate

HRID 922437노트

반응식

HRID 922437 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]=[CH:2]1.Br[CH2:15][CH2:16][CH2:17][O:18][CH3:19].[I-].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][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]=[CH:2]1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 5245511-Bromo-3-methoxypropaneHCID 639844Methyl indole-6-carboxylate

생성물 1

HCID 67542758methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate수율 82.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of methyl 1H-indole-6-carboxylate (5.0 g) in N,N-dimethylformamide (40 mL) was added dropwise a solution of 1-bromo-3-methoxypropane (5.24 g) in N,N-dimethylformamide (10 mL) under ice-cooling, and then thereto was added potassium iodide (948 mg), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was sequentially added ethyl acetate and water under ice-cooling, and the organic layer was separated. The organic layer was washed with water twice and saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1) to give methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate [REx(6-1)] (5.8 g) as a colorless oil.

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water twice
  5. dry with materialsaturated saline, dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1)

출처 및 근거

ORD 기록
ord-c7a6004ce3b0481282c49eff9bdd8cb4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278944B2

반응 노트

불러오는 중…