Methyl iodide → HCID 67227504, compound

HRID 624443Notes

Reaction equation

HRID 624443 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([O:15][C:16]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:30]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH3:30])[C:9]1[N:14]=[CH:13][C:12]([O:15][C:16]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67228575HCID 67228575, compound

Product 1

HCID 67227504HCID 67227504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EXAMPLE 377B (0.750 g) in N,N-dimethylformamide (5 mL) was added sodium hydride (0.091 g). The reaction was stirred for 30 minutes at room temperature and then iodomethane (0.142 mL) was added to the reaction and stirring was continued at room temperature for 2 hours. The reaction was quenched with water (25 mL) and extracted with ethyl acetate (75 mL). The organic layer was separated, washed with brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. The residue was loaded onto silica gel (Reveleris 40 g) and eluted with a gradient of 5-15% ethyl acetate/hexanes over 30 minutes (flow=40 ml/min) to provide the title compound.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 2 hours
  3. customThe reaction was quenched with water (25 mL)
  4. extractionextracted with ethyl acetate (75 mL)
  5. customThe organic layer was separated
  6. washwashed with brine (50 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washeluted with a gradient of 5-15% ethyl acetate/hexanes over 30 minutes (flow=40 ml/min)

Sources & evidence

ORD record
ord-48219626685942f2a42ed5cb9a855c49
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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