(E)-ethyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)acrylate → 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)propanoic acid

HRID 563381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563381
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](/[CH:18]=[CH:19]/[C:20]([O:22]CC)=[O:21])=[C:14]([CH3:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1>CCO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[C:14]([CH3:17])[CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 86640303(E)-ethyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)acrylate

Produkt 1

HCID 670052123-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)propanoic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

(c)(d) (E)-ethyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)acrylate (350 mg, 1.08 mmol) was dissolved in EtOH (30 mL) and hydrogenated over 10% Pd/C (70 mg) at 50 psi H2 for 4 h. The catalyst was filtered off and the solution was treated with 1 M NaOH (30 mL) and stirred for 16 h. The pH was adjusted to 4-5 with conc HCl. Most of the EtOH was removed in vacuo and the solution was extracted with EtOAc and dried over MgSO4, filtered, and conc. Obtained 320 mg (100%) of 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)propanoic acid.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. additionthe solution was treated with 1 M NaOH (30 mL)
  3. customMost of the EtOH was removed in vacuo
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-77889b008b734abfaf0af84e5ad87b1d
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067447B2

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