o-Toluenesulfonyl chloride → 4-Bromo-1-(2-methyl-benzenesulfonyl)-1H-indole

HRID 1159763

반응식

HRID 1159763 반응식
[OH-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](Cl)(=[O:22])=[O:21]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH3:13])(=[O:22])=[O:21]

참가 물질

7

반응물 3

HCID 8623o-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 6764944-Bromoindole

생성물 1

HCID 220153344-Bromo-1-(2-methyl-benzenesulfonyl)-1H-indole수율 54%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

Aq. 2.5 M NaOH (5 mL) was added to a stirring mixture of 4-bromo-1H-indole (1000 mg, 5.3 mmol), 2-methylbenzenesulfonyl chloride (1100 mg, 5.6 mmol) and tetrabutylammonium hydrogen sulfate (173 mg, 0.5 mmol) in DCM (10 mL). The reaction mixture was stirred at ambient temperature overnight. The mixture was diluted with DCM and water and the layers were separated. DCM was washed with water 2 times, dried (MgSO2) and concentrated to give 1.6 g of crude material that was purified using flash chromatography (SiO2, eluent EtOAc:hexane 9:1) giving the title product (1 g, 54%). MS (ESI+) for C15H12BrNO2S m/z 350 (M+H)+.

후처리

  1. customthe layers were separated
  2. washDCM was washed with water 2 times
  3. dry with materialdried (MgSO2)
  4. concentrationconcentrated
  5. customto give 1.6 g of crude material that
  6. customwas purified

출처 및 근거

ORD 기록
ord-3218029980604fa5ab77b0b0aeb011a5
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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