Trifluoroacetic acid → 5-Chloro-4-(6-cyclopropyl-5-(1,1-difluoroethoxy)pyridin-3-yloxy)-2-fluorobenzoic acid

HRID 2048120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2048120
[Cl:1][C:2]1[C:3]([O:16][C:17]2[CH:18]=[N:19][C:20]([CH:28]3[CH2:30][CH2:29]3)=[C:21]([O:23][C:24]([F:27])([F:26])[CH3:25])[CH:22]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9]C(C)(C)C)=[O:8].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([O:16][C:17]2[CH:18]=[N:19][C:20]([CH:28]3[CH2:30][CH2:29]3)=[C:21]([O:23][C:24]([F:27])([F:26])[CH3:25])[CH:22]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([OH:9])=[O:8]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 58042461HCID 58042461, Verbindung

Produkt 1

HCID 580424975-Chloro-4-(6-cyclopropyl-5-(1,1-difluoroethoxy)pyridin-3-yloxy)-2-fluorobenzoic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 5-chloro-4-(6-cyclopropyl-5-(1,1-difluoroethoxy)pyridin-3-yloxy)-2-fluorobenzoate (Preparation 270, 260 mg, 0.59 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (440 μL, 5.86 mmol). The reaction mixture was stirred over 48 hours at room temperature then concentrated in vacuo and the crude residue azeotroped with methanol (2×25 mL). The crude material was purified by silica gel column chromatography eluting with 50% ethyl acetate in heptane to afford the title compound as a white solid (200 mg, 96%).

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customthe crude residue azeotroped with methanol (2×25 mL)
  3. customThe crude material was purified by silica gel column chromatography
  4. washeluting with 50% ethyl acetate in heptane

Quellen und Nachweise

ORD-Eintrag
ord-38004ac2ae8842f6a8e06be43ed147ec
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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