Potassium Carbonate → Methyl 3-(4-methoxy-1H-pyrazol-5-yl)-4-methylbenzoate

HRID 1488140Notes

Reaction equation

HRID 1488140 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+].I[C:28]1[C:32]([O:33][CH3:34])=[CH:31][NH:30][N:29]=1>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:34][O:33][C:32]1[CH:28]=[N:29][NH:30][C:31]=1[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[CH3:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 532171365-Methoxycarbonyl-2-methylphenylboronic acid pinacol esterHCID 178493805HCID 178493805, compound2×

Product 1

HCID 90030202Methyl 3-(4-methoxy-1H-pyrazol-5-yl)-4-methylbenzoateYield 73.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Into a 50-mL three neck round-bottom flask, purged and maintained with nitrogen, was placed a solution of methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (414 mg, 1.50 mmol) in dioxane (6 mL). Potassium carbonate (2 M, 2.5 mL, 5.00 mmol), 3-iodo-4-methoxy-1H-pyrazole (compound 244.5, 224 mg, 1.00 mmol), Pd(dppf)Cl2 (73 mg, 0.10 mmol) were added to the reaction and the resulting mixture was stirred overnight at 90° C. The resulting mixture was cooled, then diluted with EtOAc (80 mL) and washed with brine (2×30 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1/1) as eluent to obtain the title compound as a yellow oil (180 mg, 73%).

Workup

  1. customInto a 50-mL three neck round-bottom flask, purged
  2. temperaturemaintained with nitrogen
  3. temperatureThe resulting mixture was cooled
  4. washwashed with brine (2×30 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by a silica gel column chromatography with ethyl acetate/petroleum ether (1/1) as eluent

Sources & evidence

ORD record
ord-0d5e1597ddb54580b8583828a9914c95
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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