4-Fluorobenzoic Acid → 5Chloro-2-(4fluorophenyl)imidazo[4,5-b]pyridine

HRID 396369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396369
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=O)=[CH:13][CH:12]=1>>[Cl:9][C:4]1[N:3]=[C:2]2[N:1]=[C:15]([C:14]3[CH:18]=[CH:19][C:11]([F:10])=[CH:12][CH:13]=3)[NH:8][C:7]2=[CH:6][CH:5]=1

Komponenten

3

Edukt 2

HCID 99734-Fluorobenzoic AcidHCID 106306156-Chloropyridine-2,3-diamine

Produkt 1

HCID 224861255Chloro-2-(4fluorophenyl)imidazo[4,5-b]pyridineAusbeute 46,6 %

Versuchsvorschrift

2,3-Diamino-6-chloropyridine (Davos-Bulk supplier, 2.25 g 15.6 mmol) and 4-fluorobenzoic acid (2.62 g 18.7 mmol) are treated with polyphosphoric acid (56.4 g) at 150° C. for 6 h. The reaction mixture is poured on ice-water/NH3conc. and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to yield the crude product, which is purified by recrystallisation from ethyl acetate/tert.butyl methyl ether to yield the title compound (1.8 g 44%) as grey crystals.

Aufarbeitung

  1. additionThe reaction mixture is poured on ice-water/NH3conc
  2. extractionand extracted with ethyl acetate three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto yield the crude product, which
  7. customis purified by recrystallisation from ethyl acetate/tert.butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-fe20243a49b742bf9cff00e9161f3605
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608072B1

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