Sodium Carbonate → HCID 87279535, compound

HRID 624460Notes

Reaction equation

HRID 624460 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-e37fe4dfc0f14395ab60a0c8626b7cd8
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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