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

HRID 383459
Notes
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Reaction equation

HRID 383459 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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

Sources & evidence

ORD record
ord-bb37a481c3a74a628cf062b8e5efb412
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367665B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes