Trifluoroacetic acid → 4-((5,6-Dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acid

HRID 512040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512040
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:23]([F:24])=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([F:25])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:23]([F:24])=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:25])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86682568tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate

Produkt 1

HCID 866825694-((5,6-Dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acidAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate (Preparation 13, 490 mg, 1.27 mmol) in DCM (5 mL) was added TFA (5 mL). After 30 minutes the reaction mixture was concentrated in vacuo and the resulting residue was purified by reverse phase chromatography eluting with H2O/MeCN/HCOOH (95/5/0.1 to 5/95/0.1, Biotage™ 40 g C18-silica gel) to yield the title compound (210 mg, 50%).

Aufarbeitung

  1. concentrationAfter 30 minutes the reaction mixture was concentrated in vacuo
  2. customthe resulting residue was purified by reverse phase chromatography
  3. washeluting with H2O/MeCN/HCOOH (95/5/0.1 to 5/95/0.1, Biotage™ 40 g C18-silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-f00bce9fb69e490a853813c9741f2d31
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102621B2

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