Potassium Phosphate, Tribasic → HCID 67272898, compound

HRID 1698543Notes

Reaction equation

HRID 1698543 reaction equation
Br[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O)[CH3:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:14]

Participants

9

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 596354707-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 67272898HCID 67272898, compoundYield 64.4%

Reagents, catalysts & solvents 5

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 280 mg (1.23 mmol) of 7-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one, 222 mg (1.48 mmol) of 2-ethylphenylboronic acid, 113 mg (0.0123 mmol) of tris(dibenzylideneacetone)dipalladium, 29 mg (0.0615 mmol) of X-Phos and 522 mg (2.46 mmol) of potassium phosphate in 9 mL of toluene was stirred at 100° C. for 4 hours. After cooling, the reaction mixture was diluted with water and ethyl acetate and passed through celite. The filtrate was extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25-65% ethylacetate/n-hexane gradient mixture to give 200 mg (64%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionThe filtrate was extracted with ethyl acetate (X2)
  3. washThe combined organic layer was washed with brine (X1)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 25-65% ethylacetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-8329c926b35c499d86bb5246c45e9d14
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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