Potassium Carbonate → methyl 3-(1-methyl-1H-pyrazol-5-yl)benzoate

HRID 2201990Notes

Reaction equation

HRID 2201990 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].Br[C:15]1[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>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].O>[CH3:20][N:19]1[C:15]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])=[CH:16][CH:17]=[N:18]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 179333815-Bromo-1-methyl-1H-pyrazole

Product 1

HCID 69687203methyl 3-(1-methyl-1H-pyrazol-5-yl)benzoateYield 83.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (270 mg, 1.5 mmol), 5-bromo-1-methyl-1H-pyrazole (200 mg, 1.25 mmol), K2CO3 (518 mg, 3.75 mmol) and Pd(dppf)Cl2 (10 mg) in a mixture solution of dioxane (8 mL) and H2O (2 mL) was stirred at 120° C. for 30 min under microwave heating. The catalyst was filtered and the filtrate concentrated. The residue was then purified by column chromatography to give provide the desired product as a colorless oil (226 mg, Yield 60%). It was used directly in the next step. LCMS (m/z): 217.1.

Workup

  1. temperatureheating
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was then purified by column chromatography
  5. customto give

Sources & evidence

ORD record
ord-3c84ec2475c9491d8310fee9fbcffafa
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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