Water → HCID 68276399, compound

HRID 1487388Notes

Reaction equation

HRID 1487388 reaction equation
[CH3:1]C([O-])(C)C.[K+].IC.[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[NH:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([S:26][CH3:27])[N:19]=1.O>CN(C)C=O>[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[N:17]([CH3:1])[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([S:26][CH3:27])[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 23665647Potassium tert-butoxideHCID 68276347HCID 68276347, compound

Product 1

HCID 68276399HCID 68276399, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.05 mL (5.04 mmol) of potassium 2-methylpropan-2-olate and then 286 μL (1.8 eq) of iodomethane are added dropwise under nitrogen to a solution of 700 mg (2.52 mmol) of 6-(2,4-difluorophenylamino)-2-(methylthio)nicotinonitrile in 20 mL of N,N-dimethyl formamide. The reaction medium is stirred at room temperature for 24 hours and then 126 μL (0.8 eq, 2.02 mmol) of iodomethane is added. The reaction medium is stirred at room temperature for 2 additional hours. Water is added and the product is extracted with ethyl acetate. The organic phase is dried on anhydrous magnesium sulfate, filtered, and evaporated to yield 660 mg (90%) of 6-((2,4-difluorophenyl)(methyl)amino)-2-(methylthio)nicotinonitrile in the form of a brown solid.

Workup

  1. stirringThe reaction medium is stirred at room temperature for 2 additional hours
  2. extractionthe product is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried on anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b0562f3f81534171845c49ad2d2bb3c3
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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