Azobisisobutyronitrile → 1-benzenesulfonyl-6-bromo-5-bromomethyl-1H-indole

HRID 221925Notes

Reaction equation

HRID 221925 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH3:20])=[C:16]([Br:19])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:20][Br:21])=[C:16]([Br:19])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 594888191-benzenesulfonyl-6-bromo-5-methyl-1H-indole

Product 1

HCID 594887781-benzenesulfonyl-6-bromo-5-bromomethyl-1H-indoleYield 46.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under a nitrogen stream, a solution of 1-benzenesulfonyl-6-bromo-5-methyl-1H-indole (40 mg, 0.11 mmol), N-bromosuccinimide (NBS) (22 mg, 0.12 mmol) and 2,2′-azobis(isobutyronitrile) (AIBN) (1 mg, 0.01 mmol) in carbon tetrachloride (0.5 mL) was heated to reflux for 1 hour. The reaction mixture was cooled to room temperature, and then purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:9)), to thereby obtain the titled compound (22 mg, 45%).

Workup

  1. temperatureto reflux for 1 hour
  2. custompurified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:9))

Sources & evidence

ORD record
ord-64eaa85cc290457c929eef04379b2e5b
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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