HCID 67654654, compound → HCID 18975318, compound

HRID 2393449Notes

Reaction equation

HRID 2393449 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:14]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][NH:12][C:9]3=[CH:10][N:11]=2)[CH:5]=1.[H][H]>[Pd].C(O)C>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:14]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][NH:12][C:9]3=[CH:10][N:11]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 67654654HCID 67654654, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18975318HCID 18975318, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-(5-(1,2,4-triazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)prop-2-enoate (0.4 g, 1.4 mmol) was hydrogenated over palladium on carbon (10%, 0.25 g) in ethanol (50 mL) at 45 psi of hydrogen for 6 hours. The catalyst was removed by filtration and the solvent evaporated in vacuo to give the title compound (0.32 g, 80%) as a colourless solid. mp 215°-218° C. 1H NMR (360 MHz, CDCl3 : d4 -MeOH 9:1) δ 1.23 (3H, t, J=7.1Hz), 2.72 (2H, t, J=7.4Hz), 3.12 (2H, t, J=7.4Hz), 4.13 (2H, q, J=7.1Hz), 7.36 (1H, s), 7.61 (1H, s), 8.60 (1H, s) and 8.89 (2H, s).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-41129b9b75b848a4af5cc6ed519620d0
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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