Methyl iodide → HCID 86686572, compound

HRID 1528091Notes

Reaction equation

HRID 1528091 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([CH2:17][CH2:16][CH2:15]1)[C:5](=[O:14])[NH:6]2.[H-].[Na+].[CH3:20]I.[Cl-].[NH4+]>CN(C=O)C>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([CH2:17][CH2:16][CH2:15]1)[C:5](=[O:14])[N:6]2[CH3:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86686573HCID 86686573, compound

Product 1

HCID 86686572HCID 86686572, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-fluoro-5′-nitrospiro[cyclobutane-1,3′-indol]-2′ (1′H)-one (300 mg) and sodium hydride (36.6 mg) in DMF (10 mL) was added methyl iodide (0.395 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr under a nitrogen atmosphere. To the reaction mixture was added saturated aqueous ammonium chloride solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (282 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-372bccdcacaa44ee953470f061596283
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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