Toluene → Ethyl 2,3-dimethyl-1H-indole-5-carboxylate

HRID 1851879Notes

Reaction equation

HRID 1851879 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:14](OC(C)(C)C)=O)N)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:21][C:22](=O)CC.[C:26]1(C)C=CC=CC=1>>[CH3:26][C:14]1[NH:12][C:9]2[C:8]([C:21]=1[CH3:22])=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=2

Participants

4

Reactant 3

HCID 1140TolueneHCID 6569Methyl Ethyl KetoneHCID 59239861HCID 59239861, compound

Product 1

HCID 612460Ethyl 2,3-dimethyl-1H-indole-5-carboxylate

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 1-(4-(ethoxycarbonyl)phenyl)hydrazinecarboxylate (5.27 g, 18.8 mmol), butan-2-one (2.53 mL, 28.2 mmol), and TsOH monohydrate (21.5 g, 112.8 mmol) in toluene (300 mL) was heated at 80° C. for 2 h. The reaction mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated and then purified by flash chromatography (AcOEt/Hexane 5%) to obtain the title compound. ESI-MS (m/z): 218 [M+H]+.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography (AcOEt/Hexane 5%)

Sources & evidence

ORD record
ord-3f7cebec4d9e42b99291d74d88d07e98
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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