Sodium hydride → 3-iodo-4-methoxy-1-(tetrahydro-3-furanyl)-1H-Pyrrolo[3,2-c]pyridine

HRID 2206008노트

반응식

HRID 2206008 반응식
[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH:26]2[CH2:30][CH2:29][O:28][CH2:27]2)(=O)=O)=CC=1>CN(C=O)C>[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:26]2[CH2:30][CH2:29][O:28][CH2:27]2)[CH:3]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateHCID 247294143-Iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

생성물 1

HCID 1179876973-iodo-4-methoxy-1-(tetrahydro-3-furanyl)-1H-Pyrrolo[3,2-c]pyridine수율 91.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine (0.100 g) in DMF (5 mL) was added sodium hydride (60% dispersion in mineral oil, 36.1 mg), and the mixture was stirred at room temperature for 1 hr. Tetrahydrofuran-3-yl 4-methylbenzenesulfonate (221 mg) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (115 mg).

후처리

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-e342b531c0c74122ad8cff64a84e05ca
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

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