Hydrochloric Acid → 4-((5-Chloro-6-isopropoxypyridin-3-yl)methoxy)-2,5-difluorobenzoic acid

HRID 1525662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525662
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:19]([F:20])=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:21])[CH:12]=2)[CH:5]=[N:6][C:7]=1Cl.[H-].[Na+].[CH3:24][CH:25]([OH:27])[CH3:26].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:19]([F:20])=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:21])[CH:12]=2)[CH:5]=[N:6][C:7]=1[O:27][CH:25]([CH3:26])[CH3:24]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 866825694-((5,6-Dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acid

Produkt 1

HCID 666679654-((5-Chloro-6-isopropoxypyridin-3-yl)methoxy)-2,5-difluorobenzoic acidAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acid (Preparation 8, 210 mg, 0.63 mmol) in THF (5 mL) was added at room temperature sodium hydride (157 mg, 6.3 mmol) followed by iPrOH (5 ml). The reaction mixture was stirred at 90° C. for 18 hours. After cooling, HCl 1M (30 mL) was added to the reaction mixture and it was extracted with ethyl acetate (2×100 mL). The combined organic layers were concentrated in vacuo and purified by reverse phase chromatography to give the title compound (105 mg, 46%).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionwas extracted with ethyl acetate (2×100 mL)
  3. concentrationThe combined organic layers were concentrated in vacuo
  4. custompurified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9cda74208d2a40a6a18adccdb388d253
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085517B2

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