Sodium Hydroxide → [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

HRID 1254857

Reaktionsgleichung

Reaktionsgleichung von HRID 1254857
[OH-].[Na+].C[O:4][C:5](=[O:24])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:8]=1[CH3:23]>C1COCC1.CO>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([N:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[C:7]([CH2:6][C:5]([OH:24])=[O:4])=[C:8]2[CH3:23])=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67220030[1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Produkt 1

HCID 11709219[1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

1M Aqueous NaOH (0.5 mL) is added to a stirring solution of [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (4 mg, 0.013 mmol) in 1:1 THF/MeOH (2 mL). After 18 hours, the reaction is evaporated and the residue dissolved in water. The aqueous solution is acidified to pH 1, and extracted with ethyl acetate. The organic layer is washed with water then brine, dried (MgSO4) then evaporated, to give [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid; MH+=301.

Aufarbeitung

  1. customthe reaction is evaporated
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customthen evaporated

Quellen und Nachweise

ORD-Eintrag
ord-dd4ce68a3afe4affb851e4199100bec2
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455645B2

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