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

HRID 22568Notes

Reaction equation

HRID 22568 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-ethoxycarbonyl-5,6,7,8-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-ea58cf6f49e94b9ca3457f4a7bddfeea
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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