methyl 4-(4-ethenyl-1-methyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate → methyl 5-ethyl-4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

HRID 2392125Notes

Reaction equation

HRID 2392125 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][N:6]([CH3:19])[C:7]=1[C:8]1[CH:9]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[S:11][C:12]=1[CH2:13][CH3:14])=[CH2:2]>CO.[Pd]>[CH2:13]([C:12]1[S:11][C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:9][C:8]=1[C:7]1[N:6]([CH3:19])[N:5]=[CH:4][C:3]=1[CH2:1][CH3:2])[CH3:14]

Participants

4

Reactant 1

HCID 57826594methyl 4-(4-ethenyl-1-methyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate

Product 1

HCID 57826489methyl 5-ethyl-4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(4-ethenyl-1-methyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate (187 mg, 0.68 mmol) in methanol (2.5 ml) was added Pd—C (7.20 mg, 0.07 mmol). The reaction mixture was hydrogenated at 1 atm (balloon) for 1 h. The solution was then purged with N2, filtered through Celite and concentrated affording methyl 5-ethyl-4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (187 mg, 0.64 mmol, 95% yield) as a clear oil which was used without further purification: LCMS (ES) m/e 279 (M+H)+.

Workup

  1. customThe solution was then purged with N2
  2. filtrationfiltered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-78a64458468045a590e29701987a0eb8
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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