Methyl iodide → HCID 178436893, compound

HRID 2105019Notes

Reaction equation

HRID 2105019 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:7]([OH:18])[C:8]2[C:9]([F:17])=[C:10]([OH:16])[CH:11]=[C:12]([CH2:14][CH3:15])[CH:13]=2)[NH:5][CH:6]=1.[C:19]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([CH:7]([C:8]2[CH:13]=[C:12]([CH2:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:19])[C:9]=2[F:17])[OH:18])[NH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178436941HCID 178436941, compound

Product 1

HCID 178436893HCID 178436893, compoundYield 154.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 206.2 (394 mg, 0.707 mmol) in 5 mL DMF at rt, were added K2CO3 (117 mg, 0.848 mmol) and iodomethane (132 μL, 2.12 mmol). The mixture was stirred at rt for 3 days, then diluted with EtOAc. The organic phase was washed with H2O (2×), sat. Na2SO3, H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 60% EtOAc/hexanes gradient) to afford 359.4 mg of Intermediate 206.3 as a colorless solid.

Workup

  1. washThe organic phase was washed with H2O (2×), sat. Na2SO3, H2O and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 60% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-410ba984305f48349514830e3f42bc49
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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