Iodoethane → Ethyl 4-chloro-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylate
Reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][N:3]=1.[H-].[Na+].[CH2:18](I)[CH3:19]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH2:18][CH3:19])[C:6]=2[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][N:3]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (0.10 g) was dissolved in dimethylformamide (2 ml), cooled to 0° C. and sodium hydride (60% dispersion in oil) (0.027 g) added. The reaction mixture was stirred for 45 minutes at 0° C., allowed to warm to room temperature and stirred for a further 45 minutes. The reaction mixture was cooled to 0° C., ethyl iodide (0.039 ml) added, the reaction mixture allowed to warm to room temperature, and stirred for 1 hour. The reaction mixture was partitioned between ethyl acetate and water, the aqueous was separated and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a yellow oil (0.095 g).
Workup
- temperatureto warm to room temperature
- stirringstirred for a further 45 minutes
- temperatureThe reaction mixture was cooled to 0° C.
- temperatureto warm to room temperature
- stirringstirred for 1 hour
- customThe reaction mixture was partitioned between ethyl acetate and water
- customthe aqueous was separated
- extractionextracted three times with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-68c73db371c745e6a5e6544bb7510df5
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589206B2
Reaction notes
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