Potassium Carbonate → 5-methoxy-1-methyl-1H-indole
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[C:12](=O)([O-])[O-].[K+].[K+].C(=O)(OC)OC>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[CH:6]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 5-methoxyindole (1 g, 6.79 mmol), potassium carbonate (0.5 g), N,N-dimethylformamide (10 mL) and dimethyl carbonate (1.7 mL, 20 mmol) was stirred and heated to reflux (˜130° C.). The progress of the reaction was monitored by HPLC. Within 5 h, the starting indole had been consumed and after the mixture was cooled to ˜3° C., it was treated with ice cold water (30 mL). The formed precipitate was filtered off, then was washed in turn with water (2×30 mL) and hexanes (30 mL). The colorless product was dried under vacuum at 25° C. for 48 h to afford 5-methoxy-1-methylindole (1.067 g, 97.4% yield).
Workup
- temperatureheated
- customthe starting indole had been consumed
- temperatureafter the mixture was cooled to ˜3° C.
- additionit was treated with ice cold water (30 mL)
- filtrationThe formed precipitate was filtered off
- washwas washed in turn with water (2×30 mL) and hexanes (30 mL)
- customThe colorless product was dried under vacuum at 25° C. for 48 h
Sources & evidence
- ORD record
- ord-aef806b8f3f24047b0756ad406dad351
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326501B1
Reaction notes
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