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

HRID 450835

반응식

HRID 450835 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 3150171-(Phenylsulfonyl)-1H-indole

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6a32503dd37d421f8a901bbb005763f0
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486991B2

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