Water → HCID 73443578, compound

HRID 992746Notes

Reaction equation

HRID 992746 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[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].[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=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>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:22]=[CH:21][CH:20]=[C:4]([O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:12](=[N:17][O:18][CH3:19])[C:13]([NH:15][CH3:16])=[O:14])[CH:3]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 73443579HCID 73443579, compound

Product 1

HCID 73443578HCID 73443578, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 13 g of the product from Example 7 in 105 ml of dimethoxyethane was admixed with 9.9 g of 4-chlorophenylboronic acid, 6.7 g of sodium carbonate, 34 ml of water and 200 mg of tetrakis(triphenylphosphine)palladium(0) and refluxed for 3 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 9.5 g of product as colorless crystals of m.p. 118-121° C.

Workup

  1. temperaturerefluxed for 3 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-1bfefa1afb4c4e1ca170a3b88a87104a
Source dataset
uspto-grants-2002_10
Patent number
US06469195B1

Reaction notes

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