Sodium hydride → 6-Chloro-2-isobutoxy-nicotinamide

HRID 1483757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483757
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].ClC1C=[CH:20][C:16]([C:17](N)=[O:18])=[C:15](OCCC)N=1.[H-].[Na+]>C(#N)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([O:18][CH2:17][CH:16]([CH3:20])[CH3:15])[N:10]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 221427782,6-Dichloropyridine-3-carboxamideHCID 579687006-Chloro-2-propoxy-nicotinamide

Produkt 1

HCID 579689596-Chloro-2-isobutoxy-nicotinamideAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dichloro-nicotinamide (1) (3 g, 15.7 mmol) in acetonitrile (anhydrous, 30 mL) were added 2-methyl-propan-1-ol (2) (1.22 g, 16.5 mmol) and NaH (0.42 g, 16.5 mmol). The reaction was kept at r.t. O/N. The suspension was filtered and the filtrate was concentrated in vacuo. The residue was purified by Biotage silica gel chromatography with 10%-80% EtOAc/hexanes gradient elution to afford 2.39 g (66% yield) of the title compound.

Aufarbeitung

  1. customwas kept at r.t
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by Biotage silica gel chromatography with 10%-80% EtOAc/hexanes gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-857961f615c54e5aa0bad7f07c169487
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416146B2

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