3-Bromophenylhydrazine hydrochloride → 3-(6-Bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

HRID 1466771Notes

Reaction equation

HRID 1466771 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH2:11][C:12](=O)[CH3:13])[CH:5]=1.Cl.[Br:17][C:18]1[CH:19]=[C:20]([NH:24]N)[CH:21]=[CH:22][CH:23]=1>CC(O)(C)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:21]3[C:20](=[CH:19][C:18]([Br:17])=[CH:23][CH:22]=3)[NH:24][C:12]=2[CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 337573-Bromophenylhydrazine hydrochlorideHCID 667650343-(2-Oxo-propylsulfanyl)-benzoic acid methyl ester

Product 1

HCID 667653623-(6-Bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

3-(2-Oxo-propylsulfanyl)-benzoic acid methyl ester (3.65 g, 16.29 mmol) and 3-bromophenylhydrazine hydrochloride (4.01 g, 17.92 mmol) were mixed together in t-BuOH (100 mL) and heated to reflux for 1 hour. After cooling the reaction was concentrated then submitted to standard workup procedure and the crude mixture was purified by silica gel chromatography (0-30% EtOAc in hexanes) to afford a separable 5:4 mixture of regioisomers wherein the title compound was the major product.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling the reaction
  4. concentrationwas concentrated
  5. customthe crude mixture was purified by silica gel chromatography (0-30% EtOAc in hexanes)
  6. customto afford

Sources & evidence

ORD record
ord-8b9caea93b454b769cccc19ab7c491e9
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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