Water → HCID 21833857, compound

HRID 1741076Notes

Reaction equation

HRID 1741076 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:13])[CH:10]=[CH:11][N:12]=2)=[CH:4][C:3]=1[CH3:14].O.B([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:14][C:3]1[CH:4]=[C:5]([C:8]2[N:9]([CH3:13])[CH:10]=[CH:11][N:12]=2)[CH:6]=[CH:7][C:2]=1[C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 21833724HCID 21833724, compound

Product 1

HCID 21833857HCID 21833857, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-(4-Bromo-3-methylphenyl)-1-methylimidazole (D89, 600 mg, 2.39 mmol) was dissolved in dimethoxyethane (15 ml) and H2O (15 ml) and treated with 4-boronobenzoic acid (397 mg, 2.39 mmol), sodium carbonate (1.01 g, 9.56 mmol), tetrakis (triphenylphosphine)palladium (O) (60 mg) and heated at reflux for 36 hours. The dimethoxyethane was removed in vacuo, the aqueous residue treated with 10% Na2CO3 (approx. 10 ml) and washed with ethyl acetate. The aqueous phase was acidified with 5N HCl and the solid that formed collected by filtration and dried in vacuo to yield the title compound as an off-white solid (620 mg, 89%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 36 hours
  3. customThe dimethoxyethane was removed in vacuo
  4. additionthe aqueous residue treated with 10% Na2CO3 (approx. 10 ml)
  5. washwashed with ethyl acetate
  6. customthe solid that formed
  7. filtrationcollected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a1537c3e319d448ebf082ceb11401ede
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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