Dichloromethane → 1-(Phenylsulfonyl)-1H-indole

HRID 450835

反応式

HRID 450835 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1C(OCC)=O.[H-].[Na+].[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ClCCl>CN(C=O)C.O>[C:17]1([S:23]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylate

生成物 1

HCID 3150171-(Phenylsulfonyl)-1H-indole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred and cooled (to about 0° C.) solution of ethyl indole-2-carboxylate 10 (1 eq.) in DMF (2 ml/mmol) under N2, was added NaH (60% in oil, 1.2 eq.) portionwise. When gas evolution stopped, benzenesulfonyl chloride (1.2 eq.) was added. The reaction mixture was stirred for about 1 hour (TLC monitoring, eluent dichloromethane); a small amount of water then was added carefully and the DMF was evaporated. The crude residue was dissolved in ethyl acetate and washed with water and brine. After drying and evaporation of the solvents, the compound was purified by chromatography on silica gel (eluent: C6H12/EtOAc 9/1 to 7/3) to give the N-phenylsulfonylindole 62c.

後処理

  1. customthe DMF was evaporated
  2. dissolutionThe crude residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. customAfter drying
  5. customevaporation of the solvents
  6. customthe compound was purified by chromatography on silica gel (eluent: C6H12/EtOAc 9/1 to 7/3)

出典と根拠

ORDレコード
ord-6a32503dd37d421f8a901bbb005763f0
出典データセット
uspto-grants-2013_07
特許番号
US08486991B2

関連ノート

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