Sodium Carbonate → HCID 87279422, compound

HRID 1045218Notes

Reaction equation

HRID 1045218 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])[CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[F:28][CH:29]([F:32])[CH2:30]I>CN(C)C=O>[F:28][CH:29]([F:32])[CH2:30][N:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:16])=[O:17])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])[CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 38335651,1-Difluoro-2-iodoethaneHCID 67126454HCID 67126454, compound

Product 1

HCID 87279422HCID 87279422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of EXAMPLE 415B (633 mg) in anhydrous N,N-dimethylformamide (10 mL) was added sodium carbonate (254 mg) and 2,2-difluoroethyl iodide (422 mg). After stirring at 110° C. for 48 hours, the mixture was concentrated. The residue was mixed with water (20 mL) and extracted with ethyl acetate. The crude product was purified on a silica gel column eluting with 10% methanol in methylene chloride to give the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was mixed with water (20 mL)
  3. extractionextracted with ethyl acetate
  4. customThe crude product was purified on a silica gel column
  5. washeluting with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-893c4c490f0440dd9d6de168995faec3
Source dataset
uspto-grants-2013_10
Patent number
US08563735B2

Reaction notes

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