Sodium Carbonate → HCID 22380736, compound

HRID 895619

Reaction equation

HRID 895619 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1OB(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1(C)C=CC=CC=1.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>[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 875218N,N-diethyl-4-iodobenzamideHCID 21940032(2-Methoxyphenyl)boric acid

Product 1

HCID 22380736HCID 22380736, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Diethylcarbamoyl-1-iodobenzene (100 mg) was dissolved in dimethoxyethane (1 ml), added with tetrakis(triphenylphosphine)palladium (19.1 mg) under argon atmosphere, and stirred at room temperature for 10 minutes. The reaction mixture was added with the solution of (2-methoxyphenyl)boric acid (100 mg) dissolved in toluene (0.5 ml) prepared above and a solution of sodium carbonate (105 mg) dissolved in water (0.5 ml) and stirred at 90° C. for 5.5 hours. The reaction mixture was added with water (2 ml) and extracted twice with dichloromethane (4 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1) to obtain 81.9 mg of the title compound. Yield: 88%.

Workup

  1. stirringstirred at 90° C. for 5.5 hours
  2. extractionextracted twice with dichloromethane (4 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-8b08b9782b2c4ddf9b3feaf5b6da48e7
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Linked notes

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