Isobutyramide → HCID 29921637, Verbindung

HRID 554767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 554767
BrC1[CH:3]=[N:4]C=C(C=1)C(O)=O.Br[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH:24]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].CC(C)C(N)=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[Zn]>[C:3]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH:24]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])#[N:4]

Komponenten

8

Edukt 3

HCID 68424IsobutyramideHCID 887075-Bromonicotinic acidHCID 18422124tert-Butyl 5-bromonicotinate

Produkt 1

HCID 29921637HCID 29921637, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 23994ZincKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 15826098HCID 15826098, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Instead of the starting material of Reference Example 56, that is, the compound S55, the 5-bromonicotinic acid was used for the similar procedure as in Reference Example 56. To the obtained tert-butyl 5-bromonicotinate (22.4 g), dimethylacetoamide (112 ml), tris(dibenzylideneacetone)dipalladium (1.59 g), zinc cyanide (6.1 g), diphenylphosphinoferrocene (1.92 g), and zinc powder (0.68 g) were added and the mixture was stirred under argon atmosphere at 120° C. for 1.5 hours. The reaction solution was filtered by sellite, which was then washed with ethyl acetate, and the filtrate was washed with saturated saline. The organic layer was dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain tert-butyl 5-cyanonicotinate (13.1 g).

Aufarbeitung

  1. filtrationThe reaction solution was filtered by sellite, which
  2. washwas then washed with ethyl acetate
  3. washthe filtrate was washed with saturated saline
  4. dry with materialThe organic layer was dried over with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-f58ad093509a4dd39e2b73cc8e2e5615
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049006B2

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