Methyl iodide → HCID 67983090, compound

HRID 870294Notes

Reaction equation

HRID 870294 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH:11]2[C:19]3[C:14](=[C:15]([F:20])[CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:21])[N:4]=1.[H-].[Na+].I[CH3:25]>C(#N)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2([CH3:25])[C:19]3[C:14](=[C:15]([F:20])[CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:21])[N:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 679824373-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-7-fluoroindolin-2-one

Product 1

HCID 67983090HCID 67983090, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

3-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one (5.0 g) is introduced as initial charge in 225 ml of acetonitrile, sodium hydride (0.73 g, 60% in mineral oil) is added and the mixture is after-stirred until a thick suspension is formed. After adding iodomethane (7.0 g), the mixture is heated to 60° C. and stirred for 11 hours at 60° C. The organic solvent is largely distilled off in vacuo. 2-Propanol is added to the partially crystalline residue and the product is filtered off. This gives the intermediate as a solid in an HPLC purity of 93% (3.46 g, 64% of theory). The structure can be confirmed by NMR spectroscopy.

Workup

  1. customis formed
  2. stirringstirred for 11 hours at 60° C
  3. distillationThe organic solvent is largely distilled off in vacuo
  4. addition2-Propanol is added to the partially crystalline residue
  5. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-1f468e9bd36944c5849fde1d36bc9256
Source dataset
uspto-grants-2015_03
Patent number
US08969553B2

Reaction notes

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