Potassium Carbonate → Methyl 1-methyl-1H-indole-3-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[C:14](=O)([O-])[O-].[K+].[K+].C(=O)(OC)OC>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[CH:6]=1)=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
Indole-3-carboxylic acid methyl ester (5.0 g, 28.54 mmol), potassium carbonate (2.5 g), N,N-dimethylformamide (35 mL) and dimethyl carbonate (7.2 mL, 85 mmol) were combined and the stirred mixture was heated to reflux (˜130° C.). Within 3.5 h, the reaction had gone to completion as determined by HPLC analysis. After the reaction mixture was cooled to ˜3° C., ice cold water (100 mL) was slowly added. The resulting slightly off-white solid was recovered by filtration and was washed with water (2×50 mL). The solid was not purified further, but was dried in vacuo at 45° C. for 24 h to provide 5.2 g of 1-methylindole-3-carboxylic acid methyl ester (96.3% yield).
Workup
- temperaturethe stirred mixture was heated
- temperatureAfter the reaction mixture was cooled to ˜3° C.
- filtrationThe resulting slightly off-white solid was recovered by filtration
- washwas washed with water (2×50 mL)
- customThe solid was not purified further
- customwas dried in vacuo at 45° C. for 24 h
Sources & evidence
- ORD record
- ord-a1568fd75e0447b481b575257b5b344f
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326501B1
Reaction notes
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