Potassium Fluoride → HCID 22485511, compound

HRID 2181321Notes

Reaction equation

HRID 2181321 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([Sn](C)(C)C)=[CH:6][C:5]=1[O:16][CH3:17])(=[O:3])[CH3:2].Cl[C:19]1[CH:24]=[CH:23][C:22]([N:25]([CH3:37])[CH2:26][CH2:27][N:28]([C:30]2[CH:31]=[CH:32][C:33](Cl)=[N:34][CH:35]=2)[CH3:29])=[CH:21][N:20]=1.[F-].[K+]>C1(C)C=CC=CC=1.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>[C:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:19]2[CH:24]=[CH:23][C:22]([N:25]([CH3:37])[CH2:26][CH2:27][N:28]([C:30]3[CH:31]=[CH:32][C:33]([C:7]4[CH:6]=[C:5]([O:16][CH3:17])[C:4]([C:1](=[O:3])[CH3:2])=[C:9]([O:10][CH3:11])[CH:8]=4)=[N:34][CH:35]=3)[CH3:29])=[CH:21][N:20]=2)=[CH:6][C:5]=1[O:16][CH3:17])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 22485520HCID 22485520, compoundHCID 22485553HCID 22485553, compound

Product 1

HCID 22485511HCID 22485511, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

Under nitrogen, to a solution of (4-acetyl-3,5-dimethoxyphenyl)trimethyltin (235.0 mg, 0.760 mmol) synthesized as described in Reference Example 8 in toluene (10 mL) were added crude N,N′-bis(2-chloro-5-pyridyl)-N,N′-dimethylethylenediamine(78.0 mg, approx. 0.25 mmol) synthesized as described in Reference Example 9 and tetrakis(triphenylphosphine)palladium (116.0 mg, 0.100 mmol). After stirring at 130° C. for 22 hours, a saturated aqueous potassium fluoride was added to the reaction mixture and the mixture was stirred for 1 hour. Insoluble materials were removed by filtration through Celite. The residue was washed with chloroform, and the aqueous layer of the filtrate was extracted with chloroform. The washing and the organic layer of the filtrate were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield N,N′-bis[2-(4-acetyl-3,5-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine as a pale yellow crystalline powder [41.4 mg, yield: 23% based on N,N′-bis(2-hydroxy-5-pyridyl)-N,N′-dimethylethylenediamine ditrifluoroacetate].

Workup

  1. customsynthesized
  2. stirringthe mixture was stirred for 1 hour
  3. customInsoluble materials were removed by filtration through Celite
  4. washThe residue was washed with chloroform
  5. extractionthe aqueous layer of the filtrate was extracted with chloroform
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8ee71965931d43dfbf5c2173c06e3705
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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