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Potassium Iodide → 5-(3-Piperidin-1-yl-propoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid Ethyl Ester

HRID 1437686
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Reaktionsgleichung

Reaktionsgleichung von HRID 1437686
[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]
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Komponenten

5

Edukt 4

HCID 4875Potassium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 684233145-(3-Chloro-propoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid Ethyl Ester

Produkt 1

HCID 684241025-(3-Piperidin-1-yl-propoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid Ethyl EsterAusbeute 68 %

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureunder reflux for 17 hours
  2. additionwas poured on water
  3. extractionwas extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was flash-chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-d5fbe9b56f66416b92a8517b95f34071
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07622466B2

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