Hydrochloric Acid → 5-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide

HRID 873321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 873321
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.[CH3:12][NH:13][O:14][CH3:15].Cl.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:9])=[N:6][CH:7]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 14232N,O-DimethylhydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 210758725-Bromo-3-fluoropyridine-2-carboxylic acid

Produkt 1

HCID 210758695-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Bromo-3-fluoropicolinic acid (1.4 g, 6.5 mmol), N,O-dimethylhydroxylamine.HCl (0.82 g, 8.45 mmol), (2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (3.2 g, 8.45 mmol) and triethylamine (2.3 mL, 16.3 mmol) were stirred in DMF (30 mL) at room temperature for 1 d. EtOAc and sat. aq. Na2CO3 solution was added and the aqueous phase extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography using silica gel and eluting with 20-80% EtOAc in isohexane to afford 5-bromo-3-fluoro-N-methoxy-N-methylpicolinamide.

Aufarbeitung

  1. extractionthe aqueous phase extracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with 20-80% EtOAc in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-df5bd44246d84c3a9b430adaa880ce09
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975406B2

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