Sodium Carbonate → HCID 21833754, compound

HRID 1741079Notes

Reaction equation

HRID 1741079 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[CH:11]=[N:10][CH:9]=2)=[CH:4][C:3]=1[CH3:14].B([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH3:14][C:3]1[CH:4]=[C:5]([C:8]2[N:12]([CH3:13])[CH:11]=[N:10][CH:9]=2)[CH:6]=[CH:7][C:2]=1[C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 21833796HCID 21833796, compound

Product 1

HCID 21833754HCID 21833754, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

5-(4-Bromo-3-methylphenyl)-1-methylimidazole (D92, 1.52 g, 6.1 mmol) was dissolved in DME (50 ml) and water (50 ml), then treated with 4-boronobenzoic acid (1.0 g, 6.1 mmol), sodium carbonate (2.57 g, 24.2 mmol) and tetrakis(triphenylphosphine)palladium (O) (100 mg). The mixture was heated at reflux (48 hours), cooled and the DME removed in vacuo. The aqueous residue was treated with 10% Na2CO3 (approx 30 ml), then washed with ethyl acetate. The aqueous phase was acidified with 5N HCl and the solid that precipitated was collected by filtration. This solid was dried in vacuo to yield the title compound as a white solid (600 mg, 34%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux (48 hours)
  3. temperaturecooled
  4. customthe DME removed in vacuo
  5. additionThe aqueous residue was treated with 10% Na2CO3 (approx 30 ml)
  6. washwashed with ethyl acetate
  7. customthe solid that precipitated
  8. filtrationwas collected by filtration
  9. customThis solid was dried in vacuo

Sources & evidence

ORD record
ord-567f4177b8964b93b496e207400c597c
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

Loading…