Methyl iodide → HCID 23441830, compound

HRID 2295086Notes

Reaction equation

HRID 2295086 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-90d51232141d4bb9be5ef1f05465a8b8
Source dataset
uspto-grants-1997_11
Patent number
US05691364

Reaction notes

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