Dimethylformamide → 5-Chloro-1-methylindole
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](C=CN2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)(OC)OC.[CH3:23][N:24]([CH3:27])[CH:25]=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:23](=[CH:9][CH:10]=1)[N:24]([CH3:27])[CH:25]=[CH:5]2Participants
5
Conditions
- Temperature
- 130 °C
Procedure
6-Chloroindole (1.0 g, 6.59 mmol), potassium carbonate (0.5 g), N,N-dimethylformamide (10 mL) and dimethyl carbonate (1.7 mL, 20.21 mmol) were stirred and heated to reflux (˜130° C.). The starting indole was consumed within 3.5 h (as determined by HPLC). After the mixture was then cooled to ˜3° C., ice cold water (50 mL) was added and the resulting oily suspension was extracted with tert-butyl methyl ether (40 mL). The separated organic layer was washed with water (3×25 mL), then was evaporated under vacuum to furnish 5-chloro-1-methylindole as a light yellow oil (1.05 g, 96.1% yield).
Workup
- temperatureheated
- customThe starting indole was consumed within 3.5 h (as determined by HPLC)
- temperatureAfter the mixture was then cooled to ˜3° C.
- additionice cold water (50 mL) was added
- extractionthe resulting oily suspension was extracted with tert-butyl methyl ether (40 mL)
- washThe separated organic layer was washed with water (3×25 mL)
- customwas evaporated under vacuum
Sources & evidence
- ORD record
- ord-5aff2a86274c4fdfaa6132a76b07298c
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326501B1
Reaction notes
Loading…