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

HRID 2290569Notes

Reaction equation

HRID 2290569 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-cyanophenylimidazo[1,5-a]pyridine hydrochloride in 5.0 ml methanol is hydrogenated at room temperature and atmospheric pressure for 30 minutes 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 5-p-cyanophenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine, 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-435acb49d36448a4aa28b40b46e924d8
Source dataset
uspto-grants-1986_10
Patent number
US04617307

Reaction notes

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