Sodium Carbonate → HCID 87279535, compound

HRID 1848939Notes

Reaction equation

HRID 1848939 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:15]([NH2:18])(=[O:17])=[O:16])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][NH:12][CH2:11]1.[F:19][CH:20]([F:23])[CH2:21]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:15]([NH2:18])(=[O:16])=[O:17])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][N:12]([CH2:21][CH:20]([F:23])[F:19])[CH2:11]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 38335651,1-Difluoro-2-iodoethaneHCID 67126487HCID 67126487, compound

Product 1

HCID 87279535HCID 87279535, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture of EXAMPLE 400B (353 mg), 1,1-difluoro-2-iodoethane (268 mg) and Na2CO3 (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 and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Flash column purification with 2.5-3% methanol/dichloromethane provided the title compound.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customFlash column purification with 2.5-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-56335ad535c54b7ea0ca38d8748632d1
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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