HCID 67171392, compound → HCID 178468660, compound

HRID 1409373Notes

Reaction equation

HRID 1409373 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2[CH:17]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:15][N:14]=2)[N:10]=[CH:9]1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.C(O)C.[Pd]>[NH:8]1[CH:12]=[C:11]([C:13]2[CH:17]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:15][N:14]=2)[N:10]=[CH:9]1

Participants

6

Reactant 2

HCID 67171392HCID 67171392, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178468660HCID 178468660, compoundYield 101.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Ethyl 3-(1-benzyl-1H-imidazol-4-yl)-1H-pyrazole-5-carboxylate (8.77 mmol, 2.6 g) was dissolved in a mixture of acetic acid (10 ml) and ethanol (190 ml). The mixture was run through H-Cube (10% Pd/C CatCart (8.77 mmol) flow 1.5 ml/min, +80° C., Full hydrogen mode). The collected fractions were combined and evaporated. The acquired solid was stirred in toluene and evaporated. This was repeated once more. 1.837 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.33 (t, 3H), 4.35 (q, 2H), 7.38 (s, 1H), 8.07 (d, 1H), 9.14 (bs, 1H), 14.44 (bs, 1H). LC-MS: [M−1]=205.0.

Workup

  1. customevaporated
  2. customevaporated

Sources & evidence

ORD record
ord-5cb25e94c7574349aba61d981f7b623e
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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