sodium thiosulfite anhydrous → 6-[(5-Fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridine-3-carbaldehyde

HRID 509960

Reaktionsgleichung

Reaktionsgleichung von HRID 509960
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[N:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.S([O-])([O-])=S.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[N:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 15847209sodium thiosulfite anhydrousHCID 58259120HCID 58259120, Verbindung

Produkt 1

HCID 866533266-[(5-Fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridine-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To {6-[(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-methanol (92, 0.353 g, 1.34 mmol) dissolved in 8 mL of tetrahydrofuran, Dess-Maritn periodinane (0.626 g, 1.47 mmol) was added and the reaction stirred at room temperature for 1 hour. The reaction was poured into aqueous saturated sodium thiosulfite and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=262.3.

Aufarbeitung

  1. additionDess-Maritn periodinane (0.626 g, 1.47 mmol) was added
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with ethyl acetate and hexane
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-510c1f871672421eba91ddc709628ff1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096593B2

Verknüpfte Notizen

Wird geladen…