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

HRID 1845482Notes

Reaction equation

HRID 1845482 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][N:6]([CH3:18])[C:7]=1[C:8]1[CH:9]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[S:11][C:12]=1[CH3:13])=[CH2:2]>CO.[Pd]>[CH2:1]([C:3]1[CH:4]=[N:5][N:6]([CH3:18])[C:7]=1[C:8]1[CH:9]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[S:11][C:12]=1[CH3:13])[CH3:2]

Participants

4

Reactant 1

HCID 57826593methyl 4-(4-ethenyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate

Product 1

HCID 57826640methyl 4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(4-ethenyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate (135 mg, 0.52 mmol) in methanol (2.6 ml) was added Pd—C (21.9 mg, 0.21 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 4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate (145 mg, 0.51 mmol, 99% yield) as a yellow oil which was used without further purification: LCMS (ES) m/e 265 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-b0b8f5625e9f4c278a312a825dfb4dab
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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