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

HRID 8130

Reaction equation

HRID 8130 reaction equation
[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]

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 220147673-(2-Nitro-2-methylpropyl)-7-nitroindole2×

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

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 IN 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%).

Workup

  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 IN 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)

Sources & evidence

ORD record
ord-fcc97bd77b3c4880aa5eed15a29d7d18
Source dataset
uspto-grants-2006_08
Patent number
US07087635B2

Linked notes

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