m-Chlorophenylhydrazine hydrochloride → 3-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1H-indole

HRID 1466762Notes

Reaction equation

HRID 1466762 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10](=O)[CH3:11])[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:14][C:15]1[CH:16]=[C:17]([NH:21]N)[CH:18]=[CH:19][CH:20]=1>CC(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[C:18]3[C:17](=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=3)[NH:21][C:10]=2[CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 628049741-((3-Bromophenyl)thio)-2-propanone

Product 1

HCID 667653273-(3-Bromo-phenylsulfanyl)-6-chloro-2-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(3-Bromo-phenylsulfanyl)-propan-2-one (1.5 g, 6.12 mmol) and 3-chlorophenylhydrazine hydrochloride (1.21 g, 6.73 mmol) were combined in t-BuOH (50 mL) and the reaction was heated to 80° C. and stirred overnight. After cooling the reaction was worked-up using standard procedures to afford a crude mixture of two regioisomers which was then purified using silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound.

Workup

  1. temperatureAfter cooling the reaction
  2. customto afford a crude
  3. additionmixture of two regioisomers which
  4. customwas then purified

Sources & evidence

ORD record
ord-3175ca7509e4468f9eeb7cdd9d05286f
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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