Methyl iodide → HCID 10615079, compound

HRID 1017219Notes

Reaction equation

HRID 1017219 reaction equation
C(C1C=C(N[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)=[C:12](C)[C:11]=2F)C=CC=1)#N.IC.[H-].[Na+].[C:32](#[N:34])[CH3:33]>>[N:15]1[C:14]([O:16][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[C:20]#[N:21])=[CH:13][CH:12]=[CH:11][C:10]=1[O:16][C:17]1[CH:18]=[CH:19][C:33]([C:32]#[N:34])=[CH:23][CH:24]=1

Participants

5

Reactant 4

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

Product 1

HCID 10615079HCID 10615079, 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-y))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-87291e95b05c4852a5c6c4672db28944
Source dataset
uspto-grants-2002_11
Patent number
US06479485B2

Reaction notes

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