Sodium Carbonate → HCID 87279442, compound

HRID 706969Notes

Reaction equation

HRID 706969 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:5]=[N:6][C:7]=1[O:8][C@@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1.[F:18][CH:19]([F:22])[CH2:20]I.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:14]([NH2:17])(=[O:15])=[O:16])[CH:5]=[N:6][C:7]=1[O:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:20][CH:19]([F:22])[F:18])[CH2:10]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 38335651,1-Difluoro-2-iodoethaneHCID 67126645HCID 67126645, compound

Product 1

HCID 87279442HCID 87279442, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of EXAMPLE 261B (353 mg), 1,1-difluoro-2-iodoethane (268 mg), sodium carbonate (283 mg) in N,N-dimethylformamide (10 mL) was heated at 80° C. overnight. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with water, brine, dried over magnesium sulfate, filtered, and concentrated. The residue was loaded onto silica gel column and eluted using a gradient of 0.5 to 3% methanol in dichloromethane to provide the title compound.

Workup

  1. washThe organic phase was washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted

Sources & evidence

ORD record
ord-cdfda0ceddb24178bf60913ea32e2e17
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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