Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-indole

HRID 551037

반응식

HRID 551037 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

참가 물질

5

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 6764944-Bromoindole

생성물 1

HCID 220153114-Bromo-1-(phenylsulfonyl)-1H-indole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-bromoindole (1.00 g, 5.10 mmol) in DMF (50 mL) at ambient temperature was added sodium hydride (220 mg of a 60% dispersion in mineral oil, 5.50 mmol). The reaction mixture was stirred for 5 min, then benzenesulfonyl chloride (901 mg, 5.10 mmol) was added and stirring was continued for 15 min. The reaction was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with CHCl3 (2×75 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 90:10, to give the title compound. MS: m/z=336 (M+1).

후처리

  1. stirringstirring
  2. waitwas continued for 15 min
  3. customThe reaction was quenched with saturated aqueous NaHCO3 (50 mL)
  4. extractionextracted with CHCl3 (2×75 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

출처 및 근거

ORD 기록
ord-c25a0b5ed9ed48e4afd66e9ad4ada2c4
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947677B2

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