Benzenesulfonyl chloride → HCID 67273214、化合物

HRID 1020915ノート

反応式

HRID 1020915 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 67273214HCID 67273214、化合物収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b47f0ec2eea14c5a800eb6a89605eeda
出典データセット
uspto-grants-2014_05
特許番号
US08716493B2

反応ノート

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