HCID 19930433, compound → 5-(p-Cyanophenyl)-3-ethoxycarbonyl5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 478007Notes

Reaction equation

HRID 478007 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:16][CH:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]>C(O)C.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:16][CH:17]=[C:13]3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 19930433HCID 19930433, compound

Product 1

HCID 199304305-(p-Cyanophenyl)-3-ethoxycarbonyl5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.1 g of 5-(p-cyanophenyl)-3-ethoxycarbonyl-imidazo[1,5-a]pyridine in 30 ml of ethanol is hydrogenated with 0.1 g of 10% Pd on charcoal at 1 bar for 2 h, filtered and evaporated to dryness. The resulting oil is partitioned between water and ethyl acetate. The organic phase is separated, dried over sodium sulfate and evaporated. The residue is chromatographed on 40 g of silica gel with ethyl acetate to yield 5-(p-cyanophenyl)-3-ethoxycarbonyl5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customThe resulting oil is partitioned between water and ethyl acetate
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on 40 g of silica gel with ethyl acetate

Sources & evidence

ORD record
ord-28d2f1bb68e04f41a20a9698829102ba
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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