Benzenesulfonyl chloride → 3-(2-Nitro-2-methylpropyl)-7-benzenesulfonamidyl-indole

HRID 1272252

반응식

HRID 1272252 반응식
[N+:1]([C:4]([CH3:19])([CH3:18])[CH2:5][C:6]1[C:14]2[C:9](=[C:10]([N+:15]([O-])=O)[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)([O-:3])=[O:2].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.N1C=CC=CC=1.[Pd]>[N+:1]([C:4]([CH3:19])([CH3:18])[CH2:5][C:6]1[C:14]2[C:9](=[C:10]([NH:15][S:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:28])=[O:27])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)([O-:3])=[O:2]

참가 물질

6

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 220147673-(2-Nitro-2-methylpropyl)-7-nitroindole2회

생성물 1

HCID 695166053-(2-Nitro-2-methylpropyl)-7-benzenesulfonamidyl-indole수율 71%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

3-(2-Nitro-2-methylpropyl)-7-nitroindole (1.89 g, 7.2 mmol) is dissolved in ethyl acetate (75 mL) and 10% Pd/C is added (750 mg). The mixture is stirred under a balloon of nitrogen for 2–3 hours. The mixture is filtered to remove the Pd/C, and the filtrate is evaporated to give a crude oil. This crude 3-(2-nitro-2-methylpropyl)-7-aminoindole is immediately dissolved in pyridine (100 mL) and the solution is cooled with an ice bath to 0° C. Benzenesulfonyl chloride is added slowly, and the mixture is stirred for 5 minutes at this temperature before removing the ice bath. The reaction mixture is stirred overnight before being quenched by addition of 1N HCl and ethyl acetate. The aqueous layer is extracted with ethyl acetate several times and the combined organic extracts are washed twice with brine and dried over Na2SO4 to give a crude oil. The crude material is purified by flash chromatography (25% ethyl acetate/hexanes) to provide 1.9 g of 3-(2-nitro-2-methylpropyl)-7-benzenesulfonamidyl-indole (71%).

후처리

  1. filtrationThe mixture is filtered
  2. customto remove the Pd/C
  3. customthe filtrate is evaporated
  4. customto give a crude oil
  5. stirringthe mixture is stirred for 5 minutes at this temperature
  6. custombefore removing the ice bath
  7. stirringThe reaction mixture is stirred overnight
  8. custombefore being quenched by addition of 1N HCl and ethyl acetate
  9. extractionThe aqueous layer is extracted with ethyl acetate several times
  10. washthe combined organic extracts are washed twice with brine
  11. dry with materialdried over Na2SO4
  12. customto give a crude oil
  13. customThe crude material is purified by flash chromatography (25% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-f43c53e9596c41b49e2ed7eeff0a67bd
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208505B2

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