Methyl iodide → HCID 57899011, compound

HRID 911023Notes

Reaction equation

HRID 911023 reaction equation
IC.[F:3][C:4]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:5]=1[O:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH3:19])[N:18]=2)[N:10]=[CH:9][C:8]=1[OH:20].[C:26](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:3][C:4]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:5]=1[O:6][C:7]1[C:8]([O:20][CH3:26])=[CH:9][N:10]=[C:11]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH3:19])[N:18]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24826839HCID 24826839, compound

Product 1

HCID 57899011HCID 57899011, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (0.0362 g, 0.255 mmol) is added to a mixture of 4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ol (0.255 mmol and potassium carbonate (0.0794 g, 0.574 mmol) in DMF (3 mL) and stirred overnight at room temperature. The reaction mixture is partitioned between water and ether. The organic layer is washed with water, dried, and concentrated. The residue is purified by silica gel chromatography, eluting with 15-20% EtOAc in hexanes, to afford N-(4-(2,6-difluorophenoxy)-5-methoxypyridin-2-yl)-4-methylthiazol-2-amine.

Workup

  1. customThe reaction mixture is partitioned between water and ether
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with 15-20% EtOAc in hexanes

Sources & evidence

ORD record
ord-40bb934ac4aa4ca68512e73ce89a3e82
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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