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

HRID 1466771

반응식

HRID 1466771 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b9caea93b454b769cccc19ab7c491e9
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000025B2

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