Methyl iodide → HCID 58244054, compound

HRID 389158Notes

Reaction equation

HRID 389158 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:31]=[C:30]([F:32])[C:7]([O:8][C:9]([C:12]2[N:13]([CH:27]([CH3:29])[CH3:28])[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[NH:21][CH2:20]4)=[N:15][N:16]=2)([CH3:11])[CH3:10])=[C:6]([F:33])[CH:5]=1.I[CH3:35]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([F:33])[C:7]([O:8][C:9]([C:12]2[N:13]([CH:27]([CH3:29])[CH3:28])[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[N:21]([CH3:35])[CH2:20]4)=[N:15][N:16]=2)([CH3:10])[CH3:11])=[C:30]([F:32])[CH:31]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58244057HCID 58244057, compound

Product 1

HCID 58244054HCID 58244054, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (55% mineral oil, 30 mg) was added to a mixture of 5-{5-[1-(4-chloro-2,6-difluorophenoxy)-1-methylethyl]-4-isopropyl-4H-1,2,4-triazol-3-yl}isoindolin-1-one (200 mg) and DMF (5 ml) under ice cooling, followed by stirring for one hour, iodomethane (0.084 ml) was added thereto, followed by stirring for one hour, while slowly elevating to room temperature. The reaction solution was concentrated, water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10) and then was solidified from ethyl acetate-diisopropylether, and the solid was collected by filtration, washed with diisopropylether and then dried under reduced pressure to obtain 5-{5-[1-(4-chloro-2,6-difluorophenoxy)-1-methylethyl]-4-isopropyl-4H-1,2,4-triazol-3-yl}-2-methylisoindolin-1-one (111 mg) as a light yellow solid.

Workup

  1. stirringby stirring for one hour
  2. customwhile slowly elevating to room temperature
  3. concentrationThe reaction solution was concentrated
  4. additionwater was added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was then evaporated
  9. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10)
  10. filtrationthe solid was collected by filtration
  11. washwashed with diisopropylether
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-970e9c0e4eaf49c0b96f24b017faf761
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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