Methyl iodide → HCID 121297562, compound

HRID 522231Notes

Reaction equation

HRID 522231 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[Br:16])([CH3:4])([CH3:3])[CH3:2].[C:18](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[C:1]([O:5][C:6](=[O:17])[N:7]([C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[Br:16])[CH3:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 125470323HCID 125470323, compound

Product 1

HCID 121297562HCID 121297562, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 144A (12.37 g, 40.1 mmol) in anhydrous N,N-dimethylformamide (100 mL) was added cesium carbonate (19.62 g, 60.2 mmol) and iodomethane (5.02 mL, 80 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 hours, and was partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated and the residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane) to provide the title compound. MS (ESI+) m/z 322 (M+1).

Workup

  1. customwas partitioned between ethyl acetate and brine
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a8117f8c22924dcaabbb5425a1716c79
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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