Hydrochloric Acid → HCID 23502816, compound

HRID 1835362Notes

Reaction equation

HRID 1835362 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](I)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:36]([O:38]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:37].Cl.[OH-].[Na+].[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>[C:36]([C:21]1[N:20]=[CH:19][C:18]([N:16]([CH3:17])[C:14](=[O:15])[C:13]([C:5]2[CH:4]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=2)([CH3:33])[CH3:32])=[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH:22]=1)(=[O:38])[CH3:37]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 23502817HCID 23502817, compound

Product 1

HCID 23502816HCID 23502816, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 300 mg (0.495 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(6-iodo-4-o-tolyl-pyridin-3-yl)-N-methyl-isobutyramide (Example 27) and 0.20 ml (0.59 mmol) 1-ethoxyvinyltri-n-butyltin in 1 ml toluene was deoxygenated by three freeze-thaw cycles. After addition of 17 mg (0.025 mmol) bis(triphenylphosphine)palladium(II) chloride the reaction mixture was heated at reflux for 16 h. Cooling to room temperature was followed by addition of 1 ml 2 M aqueous hydrochloric acid solution. After 15 min 2 ml 1N aqueous sodium hydroxide solution and 35 mg (0.59 mmol) potassium fluoride were added, followed by extraction with four portions of ethyl acetate. The combined organic layers were washed with brine, dried with magnesium sulfate and concentrated. Column chromatography afforded 147 mg (57%) of the title compound as a colorless gum.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. extractionfollowed by extraction with four portions of ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-546b45a6fbec4e3db50c7056faaa630f
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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