Potassium Fluoride → HCID 23502857, compound

HRID 1835363Notes

Reaction equation

HRID 1835363 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](I)=[N:11][CH:10]=1.[CH2:34]([O:36][C:37]([Sn](CCCC)(CCCC)CCCC)=[CH2:38])[CH3:35].[F-].[K+]>C1(C)C=CC=CC=1.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>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:34]([O:36][CH2:37][CH3:38])=[CH2:35])=[N:11][CH:10]=1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 10231844N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide

Product 1

HCID 23502857HCID 23502857, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1.00 g (1.73 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4) and 0.61 ml (1.8 mmol) 1-ethoxyvinyltri-n-butyltin in 5 ml toluene was deoxygenated by three freeze-thaw cycles. After addition of 61 mg (0.087 mmol) bis(triphenylphosphine)palladium(II) chloride the reaction mixture was heated at reflux for 16 h. The mixture was cooled to room temperature, treated with 500 mg (2.25 mmol) potassium fluoride on aluminum oxide (5.5 mmol fluoride/g) and stirred for 15 min. After filtration and washing with toluene the filtrate was concentrated. Column chromatography afforded 592 mg (66%) of the title compound as a light yellow foam.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. filtrationAfter filtration
  4. washwashing with toluene the filtrate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-48d20832f2334841a7101680db96c3b0
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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