5-(p-Cyanophenyl)imidazo[1,5-a]pyridine hydrochloride → Fadrozole

HRID 22547

Reaktionsgleichung

Reaktionsgleichung von HRID 22547
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)#[N:3]>CO.[Pd]>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1)#[N:3]

Komponenten

4

Edukt 1

HCID 199304145-(p-Cyanophenyl)imidazo[1,5-a]pyridine hydrochloride

Produkt 1

HCID 59693Fadrozole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 54 mg of 5-(p-cyanophenyl)imidazo[1,5-a]pyridine hydrochloride in 5.0 ml methanol is hydrogenated at room temperature and atmospheric pressure for 30 min with 0.1 g of 10% palladium on charcoal. The catalyst is filtered and 0.21 ml of 1N sodium hydroxide is added. The filtrate is evaporated, taken up in 10 ml of methylene chloride and filtered through Celite®. Evaporation yields an oil which is chromatographed on silica gel with ethyl acetate to yield the title compound, m.p. 117°-118°.

Aufarbeitung

  1. customis hydrogenated at room temperature
  2. filtrationThe catalyst is filtered
  3. addition0.21 ml of 1N sodium hydroxide is added
  4. customThe filtrate is evaporated
  5. filtrationfiltered through Celite®
  6. customEvaporation
  7. customyields an oil which
  8. customis chromatographed on silica gel with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8a23494cdaa649afb524d0557bf17ef6
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428160

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