Methyl iodide → HCID 86712396, compound

HRID 2174192Notes

Reaction equation

HRID 2174192 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([O:13][C:14]1[C:15]([C:20]([OH:23])([CH3:22])[CH3:21])=[N:16][CH:17]=[CH:18][CH:19]=1)=[CH:7]2.[CH3:24]I.[H-].[Na+]>CN(C)C=O>[CH3:24][O:23][C:20]([C:15]1[C:14]([O:13][C:8]2[C:9]([CH3:12])=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86712395HCID 86712395, compound

Product 1

HCID 86712396HCID 86712396, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.50 g of 2-[(8-fluoro-2-methylquinolin-3-yloxy)pyridin-2-yl]propan-2-ol and 0.45 g of methyl iodide were dissolved in 10 ml of dimethylformamide. 64 mg of sodium hydride (60% oil suspension) were added thereto while cooling with ice followed by stirring the reaction solution for 2 hours while continuing to cool with ice. Subsequently, the reaction solution was poured in ice water followed by extraction with ethyl acetate. The extract was washed with saturated saline and dried with magnesium sulfate followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 0.15 g of 3-[2-(2-methoxy-2-propyl)pyridin-3-yloxy]-8-fluoro-2-methylquinoline.

Workup

  1. temperaturewhile cooling with ice
  2. temperatureto cool with ice
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with saturated saline
  5. dry with materialdried with magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c27cfbbdaefa435a84b8cbd1d76006d1
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

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