Water → 2-bromo-1-(4-methoxyphenyl)-3-(methylthio)-1H-indole

HRID 241620Notes

Reaction equation

HRID 241620 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([S:26][CH3:27])=[CH:18]2)=[CH:13][CH:12]=1.O.C(Cl)Cl>CN(C=O)C>[Br:8][C:18]1[N:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[C:25]2[C:20]([C:19]=1[S:26][CH3:27])=[CH:21][CH:22]=[CH:23][CH:24]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 583782351-(4-methoxyphenyl)-3-(methylthio)-1H-indole

Product 1

HCID 583782112-bromo-1-(4-methoxyphenyl)-3-(methylthio)-1H-indoleYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (529 mg, 2.97 mmol) was added to a cooled (0° C.) solution of 1-(4-methoxyphenyl)-3-(methylthio)-1H-indole (800 mg, 2.97 mmol) in 10 ml of DMF. The temperature was allowed to warm to RT and the mixture was stirred at RT for 30 min. Water and DCM were added and the phases were separated. After evaporation of the solvents, the residue was purified by flash chromatography with heptane/EtAc 20:1 to provide 2-bromo-1-(4-methoxyphenyl)-3-(methylthio)-1H-indole in 66% yield. ES/MS m/z: 348.04, 350.01 (M+H).

Workup

  1. customthe phases were separated
  2. customAfter evaporation of the solvents
  3. customthe residue was purified by flash chromatography with heptane/EtAc 20:1

Sources & evidence

ORD record
ord-0e1e191ee60349cca43b2b0efeddfadb
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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