Water → HCID 72797933, compound

HRID 992745Notes

Reaction equation

HRID 992745 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[F:23])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:17][O:18][CH3:19])[C:13]([NH:15][CH3:16])=[O:14].[CH3:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.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>[F:23][C:22]1[C:2]([C:28]2[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][CH:27]=2)=[CH:3][C:4]([O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:12](=[N:17][O:18][CH3:19])[C:13]([NH:15][CH3:16])=[O:14])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 72834811HCID 72834811, compound

Product 1

HCID 72797933HCID 72797933, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 0.3 g of the product from Example 3 in 15 ml of dimethoxyethane was admixed with 0.2 g of 4-methylphenylboronic acid, 0.17 g of sodium carbonate, 2 ml of water and 40 mg of tetrakis(triphenylphosphine)palladium(0) and refluxed for 20 hours. The mixture was then poured into water and extracted with ethyl acetate, and the extract was washed with 1N aqueous sodium hydroxide solution and then with water and dried. Distillative removal of the solvent and silica gel chromatography (MtBE: cyclohexane=9:1) gave 0.3 g of the title compound.

Workup

  1. temperaturerefluxed for 20 hours
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with 1N aqueous sodium hydroxide solution
  4. dry with materialwith water and dried
  5. customDistillative removal of the solvent and silica gel chromatography (MtBE: cyclohexane=9:1)

Sources & evidence

ORD record
ord-f9d2b92edbc44897a561e06e4af5b0d5
Source dataset
uspto-grants-2002_10
Patent number
US06469195B1

Reaction notes

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