2-Chloronicotinic acid → 2-(2-Chloropyridin-3-YL)-5,6-difluoro-1H-benzo[D]imidazole

HRID 1875720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875720
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=O.[F:11][C:12]1[CH:13]=[C:14]([NH2:20])[C:15]([NH2:19])=[CH:16][C:17]=1[F:18]>>[Cl:1][C:2]1[C:3]([C:4]2[NH:19][C:15]3[CH:16]=[C:17]([F:18])[C:12]([F:11])=[CH:13][C:14]=3[N:20]=2)=[CH:7][CH:8]=[CH:9][N:10]=1

Komponenten

3

Edukt 2

HCID 762582-Chloronicotinic acidHCID 27367551,2-Diamino-4,5-difluorobenzene

Produkt 1

HCID 717418032-(2-Chloropyridin-3-YL)-5,6-difluoro-1H-benzo[D]imidazoleAusbeute 48 %

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To a suspension of 2-chloro-nicotinic acid (4.10 g, 0.026 mol; CAS Reg. No. 2942-59-8) in polyphosphoric acid (50 g) was added 4,5-difluoro-benzene-1,2-diamine (3.86 g, 0.026 mol; CAS Reg. No. 76179-40-3) and the resulting mixture was heated to 180° C. for 1 h. The reaction mixture was then cooled and neutralized with ice cold 10% aqueous sodium carbonate solution, and then extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude residue thus obtained was purified by column chromatography over silica gel (25% ethyl acetate/n-hexane) to give the title compound as a brown solid (48%). MS (Turbo Spray): m/z=266.1 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue thus obtained
  7. customwas purified by column chromatography over silica gel (25% ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-66684b27e5e5476aaf7d2b8bd545f6cb
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309581B2

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