Potassium Carbonate → HCID 18472441, compound

HRID 1387948Notes

Reaction equation

HRID 1387948 reaction equation
[CH3:1][N:2]([O:11][CH3:12])[C:3]([C:5]1[O:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].B([O-])([O-])O[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]([O:11][CH3:12])[C:3]([C:5]1[O:6][C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18472462HCID 18472462, compoundHCID 866453334-Methylphenyl borate

Product 1

HCID 18472441HCID 18472441, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 66602552Toluene-ethanol waterSolvent

Procedure

Under argon atmosphere, a solution of N-methyl-N-methoxy-5-bromofuran-2-carboxamide (2.77 g), 4-methylphenyl borate (1.93 g) and potassium carbonate (3.27 g) in toluene-ethanol-water (110-11-11 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.41 g), and the mixture was refluxed for 20 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:5→1:2→1:1) to give N-methyl-N-methoxy-5-(4-methylphenyl)furan-2-carboxamide (2.65 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1:5→1:2→1:1)

Sources & evidence

ORD record
ord-a53a162d8a024cb580bfe2caa460f8dc
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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