Methyl iodide → HCID 23441830, compound

HRID 1636396Notes

Reaction equation

HRID 1636396 reaction equation
C(C1C=[C:5]([NH:9][C:10]2[N:15]=[C:14]([O:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[C:13]([F:25])=[C:12]([CH3:26])[C:11]=2[F:27])C=CC=1)#N.IC.[H-].[Na+].[C:32](#[N:34])[CH3:33]>>[C:32]([C:33]1[CH:10]=[C:11]([CH2:5][NH:9][C:10]2[N:15]=[C:14]([O:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[C:13]([F:25])=[C:12]([CH3:26])[C:11]=2[F:27])[CH:12]=[CH:13][CH:14]=1)#[N:34]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 10666339HCID 10666339, compound

Product 1

HCID 23441830HCID 23441830, compound

Procedure

To 3-[(6-(3-cyanophenyl)amino-3,5-difluoro-4-methylpyridin-2-yl)oxy]benzonitrile (0.10 g, 0.28 mmol) in acetonitrile (10 mL) was added iodomethane (0.20 g, 1.4 mmol) and sodium hydride (0.055 g, 1.4 mmol). After stirring for 18 hours the reaction was partitioned with water and ethyl acetate. The organic layer was separated, dried (Na2SO4), and the solvent was removed in vacuo. Chromatography of the residue on silica gel with ethyl acetate/hexane (1/3) as eluent gave 3-[(6-(3-cyanophenyl)methylamino-3,5-difluoro-4-methylpyridin-2-yl)oxy]benzonitrile; NMR (CDCl3) 7.4 (m,5), 7.25 (m,1), 7.1 (m,2), 3.25 (s,3), 2.3 (s,3) ppm.

Workup

  1. customwas partitioned with water and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fdface4bd4f24e1f8ac9f2efc0f289a1
Source dataset
uspto-grants-2000_03
Patent number
US06034103

Reaction notes

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