Potassium Hydroxide → 5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[3,2-b]pyridine
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][NH:11][C:6]2=[CH:5][CH:4]=1.[OH-].[K+].O.Cl.[NH:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1>>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:19]3[CH2:20][CH2:21][NH:16][CH2:17][CH:18]=3)=[CH:10][NH:11][C:6]2=[CH:5][CH:4]=1Participants
Procedure
A solution of 0.20 gm (1.35 mMol) of 5-methoxypyrrolo-[3,2-b]pyridine, 0.23 mg (4.05 mMol) potassium hydroxide, and 0.31 gm (2.03 mMol) 4-piperidone hydrochloride monohydrate 5 mL methanol was heated at reflux for 18 hours. The reaction mixture was then concentrated under reduced pressure and the residue partitioned between water and 3:1 chloroform:isopropanol. The organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to radial chromatography chromatography (2 mm silica gel plate) eluting with dichloromethane containing 20-40% methanol and 1% ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to provide 0.21 gm (68%) of the title compound as a yellow sold. An analytical sample was crystallized from methanol.
Workup
- temperatureat reflux for 18 hours
- concentrationThe reaction mixture was then concentrated under reduced pressure
- customthe residue partitioned between water and 3:1 chloroform
- washThe organic phase was washed with saturated aqueous sodium chloride
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- washeluting with dichloromethane containing 20-40% methanol and 1% ammonium hydroxide
- additionFractions containing product
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2be75e3d6d8c493e85d7e2f2e9294d29
- Source dataset
- uspto-grants-1999_05
- Patent number
- US05905084
Reaction notes
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