Water → 5-Bromo-1-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-yl amine

HRID 18696Notes

Reaction equation

HRID 18696 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-])=O)[CH:10]=1)[N:7]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6][CH2:5]2.[Cl-].[NH4+].O>C(O)(C)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH2:11])[CH:10]=1)[N:7]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 686126655-Bromo-1-(4-methoxybenzenesulfonyl)-7-nitroindoline

Product 1

HCID 686102325-Bromo-1-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-yl amineYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 17 (9 g, 0.021 mol), iron (3.65 g, 0.065 mol), and ammonium chloride (2.33 g, 0.043 mol) in isopropanol (200 ml)-water (50 ml) was stirred at 100° C. for 4 h. After cooling, the reaction mixture was filtrated and extracted with CH2Cl2. The combined organic layer was dried by MgSO4 and evaporated to give a residue that was purified by silica gel flash column chromatography (EtOAc:n-hexane=2:3) to afford compound 18, yield 89%.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtrated
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layer was dried by MgSO4
  5. customevaporated
  6. customto give a residue that
  7. customwas purified by silica gel flash column chromatography (EtOAc:n-hexane=2:3)

Sources & evidence

ORD record
ord-ae54213838fd4403b8d5766190111df7
Source dataset
uspto-grants-2010_06
Patent number
US07741495B2

Reaction notes

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