Potassium Carbonate → 3-[1-(4-Chloro-benzyl)-5-(pyridin-2-ylmethoxy)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester

HRID 1713432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713432
[CH2:1]([O:3][C:4](=[O:27])[C:5]([CH3:26])([CH3:25])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:14]2[C:9](=[N:10][C:11]([OH:24])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].Cl[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:3][C:4](=[O:27])[C:5]([CH3:26])([CH3:25])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:14]2[C:9](=[N:10][C:11]([O:24][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 23393Picolyl chlorideHCID 178471285HCID 178471285, Verbindung

Produkt 1

HCID 597547723-[1-(4-Chloro-benzyl)-5-(pyridin-2-ylmethoxy)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

3-[1-(4-Chlorobenzyl)-5-hydroxy-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester (0.100 g, 0.26 mmol) was dissolved in acetone (2 mL), and 2-chloromethyl-pyridine (0.064 g, 0.39 mmol), tetrabutylammonium iodide (0.095 g, 0.26 mmol) and K2CO3 (0.107 g, 0.77 mol) were added. The mixture was stirred at 65° C. overnight, and two products were observed by TLC analysis. The reaction was cooled to room temperature, diluted with water, and extracted with EtOAc three times. The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated to give a 1:2 mixture of the O-alkylated and N-alkylated products. The crude material was purified by preparative TLC to obtain the O-alkylated title compound.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give
  8. additiona 1:2 mixture of the O-alkylated and N-alkylated products
  9. customThe crude material was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-40208653b2ef48a29914d934a9518560
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795274B2

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