Benzenesulfonyl chloride → HCID 67273214, 화합물

HRID 1020915노트

반응식

HRID 1020915 반응식
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[H-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[C:16]1([S:22]([N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 19616134,5-dimethoxy-1H-indole

생성물 1

HCID 67273214HCID 67273214, 화합물수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 4,5-dimethoxyindole (241 mg, 1.36 mmol) in 5 mL THF at 0° C. was added 82 mg (2.04 mmol, 1.5 eq) of sodium hydride, followed by benzenesulfonyl chloride (260 μL, 2.04 mmol, 1.5 eq). The reaction was warmed to room temperature over 5 h then quenched with H2O and concentrated. The residue was dissolved in CH2Cl2 and extracted with NaHCO3, H2O, aqueous NaCl, dried (Na2SO4), and concentrated. The product was purified by silica gel column chromatography (7/3 hexanes/EtOAc) to give 369 mg of 1-benzenesulfonyl-4,5-dimethoxy-1H-indole (86%).

후처리

  1. customthen quenched with H2O
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. extractionextracted with NaHCO3, H2O, aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe product was purified by silica gel column chromatography (7/3 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-b47f0ec2eea14c5a800eb6a89605eeda
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716493B2

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