Potassium Iodide → 5-(3-Piperidin-1-yl-propoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid Ethyl Ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:19][C:9]2=[N:10][CH:11]=[C:12]([O:14][CH2:15][CH2:16][CH2:17]Cl)[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH2:1]([O:3][C:4]([C:6]1[NH:19][C:9]2=[N:10][CH:11]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2]Participants
5
Procedure
The suspension consistent of 0.20 g (0.71 mmol) 5-(3-chloro-propoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester, 0.12 g (0.85 mmol) potassium carbonate, 0.12 g (0.71 mmol) potassium iodide and 84 ml (72 μg, 0.85 mmol) piperidine was heated under reflux for 17 hours. After cooling down to room temperature the reaction mixture was poured on water and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant to give 0.16 g (68%) of the desired compound as a light yellow solid.
Workup
- temperatureunder reflux for 17 hours
- additionwas poured on water
- extractionwas extracted three times with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe residue was flash-chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant
Sources & evidence
- ORD record
- ord-d5fbe9b56f66416b92a8517b95f34071
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622466B2
Reaction notes
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