Water → HCID 22132646, compound

HRID 1857228Notes

Reaction equation

HRID 1857228 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1.[C:23]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].O>C(Cl)(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:31]([C:30]2[CH:34]=[CH:35][C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:28][CH:29]=2)=[O:32])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 743724-tert-Butylbenzoyl chlorideHCID 22132632HCID 22132632, compound

Product 1

HCID 22132646HCID 22132646, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6212ChloroformSolvent

Procedure

6,7-Dimethoxy-4-tri-n-butylstanniophenylmethyl)quinoline (82 mg) obtained in Example 162, commercially available 4-t-butylbenzoyl chloride (31 mg) and a catalytic amount of commercially available bis(triphenylphosphine)palladium(II) chloride were dissolved in chloroform (3 ml), and the admixture was stirred for 15 hours under reflux with heat. After the addition of water, the admixture was extracted with methylene chloride, and the organic layer was washed with brine and saturated aqueous potassium fluoride and then dried with anhydrous sodium sulfate. After removing the solvent by distillation, the resulting residue was purified by thin layer chromatography on silica gel eluting with hexane/ethyl acetate (2/1) to obtain 6 mg of the title compound (yield: 10%).

Workup

  1. temperatureunder reflux
  2. temperaturewith heat
  3. extractionthe admixture was extracted with methylene chloride
  4. washthe organic layer was washed with brine and saturated aqueous potassium fluoride
  5. dry with materialdried with anhydrous sodium sulfate
  6. customAfter removing the solvent
  7. distillationby distillation
  8. customthe resulting residue was purified by thin layer chromatography on silica gel eluting with hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-a9d780c6dbe848c1a88e9779b92b452b
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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