Allyl chloride → 6-(4-Fluorophenyl)-5-[4-(methylthio)phenyl]-2-[(2-propenyl)oxy]pyridine-3-carbonitrile

HRID 2293478Notes

Reaction equation

HRID 2293478 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:14])[C:11]([C:15]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.[CH2:25](Cl)[CH:26]=[CH2:27]>CC(C)=O.C(=O)([O-])[O-].[Ag+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([O:14][CH2:27][CH:26]=[CH2:25])[C:11]([C:15]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:18]=[CH:19][C:20]([S:23][CH3:24])=[CH:21][CH:22]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7850Allyl chlorideHCID 154085741,2-Dihydro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile

Product 1

HCID 538848596-(4-Fluorophenyl)-5-[4-(methylthio)phenyl]-2-[(2-propenyl)oxy]pyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 180AcetoneSolvent

Procedure

6-(4-Fluorophenyl)-1,2-dihydro-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile (Example 1, Step 5) (100 mg, 0.297 mMol), silver carbonate (82 mg, 0.297 mMol) and allyl chloride were stirred in a brown vessel in acetone (25 ml) for 48 hours. The reaction mixture was filtered. The filtrate was condensed to give the crude compound as a solid. 6-(4-Fluorophenyl)-5-[4-(methylthio)phenyl]-2-[(2-propenyl)oxy]-pyridine-3-carbonitrile was purified by silica gel chromatography and recrystallized from hexane. Anal. Calc'd. for C22H17N2OSF: C, 70.19; H, 4.55; N, 7.44. Found: C, 69.80; H, 4.60; N, 7.32.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed

Sources & evidence

ORD record
ord-59e6549966f54084abe660cbc1c4cb96
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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