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

HRID 568539Notes

Reaction equation

HRID 568539 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

HCID 59693Fadrozole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-eaa1ad39bfc441aa963c5a7294f6950f
Source dataset
uspto-grants-1988_03
Patent number
US04728645

Reaction notes

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