Tributylstannane → 1-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-ylamine

HRID 18697Notes

Reaction equation

HRID 18697 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH2:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:6][CH2:5]2.CC(N=NC(C#N)(C)C)(C#N)C.CCCC[SnH](CCCC)CCCC>C1(C)C=CC=CC=1>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([N:7]2[C:8]3[C:4](=[CH:3][CH:2]=[CH:10][C:9]=3[NH2:11])[CH2:5][CH2:6]2)(=[O:13])=[O:14])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 686102325-Bromo-1-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-yl amine

Product 1

HCID 247482541-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-ylamineYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 18 (2 g, 4.84 mmol), AIBN (0.08 g, 0.48 mmol), Bu3SnH (3.91 ml, 14.50 mmol) in toluene (49 ml) was heated to reflux for 15 h. After cooling, the reaction mixture was evaporated and then extracted by CH2Cl2. The combined organic layer was dried by MgSO4 and concentrated to give a residue that was purified by silica gel flash column chromatography (EtOAc:n-hexane=1:2) to give compound 19, yield 90%.

Workup

  1. temperatureto reflux for 15 h
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. extractionextracted by CH2Cl2
  5. dry with materialThe combined organic layer was dried by MgSO4
  6. concentrationconcentrated
  7. customto give a residue that
  8. customwas purified by silica gel flash column chromatography (EtOAc:n-hexane=1:2)

Sources & evidence

ORD record
ord-3196d557fb8848f3bf1af18536d3e07f
Source dataset
uspto-grants-2010_06
Patent number
US07741495B2

Reaction notes

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