Iodoethane → HCID 21075345, compound

HRID 1373699Notes

Reaction equation

HRID 1373699 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[OH:27])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].C([O-])([O-])=O.[K+].[K+].[CH2:35](I)[CH3:36]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[O:27][CH2:35][CH3:36])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21075346HCID 21075346, compound

Product 1

HCID 21075345HCID 21075345, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In a 4 mL screw cap vial fitted with a small egg-shaped stir bar, were combined 5-fluoro-2-(4-fluoro-2-hydroxybenzoylamino)-N-(5-chloropyridin-2-yl)benzamide (200 mg, 0.49 mmol) and powdered anhydrous K2CO3 (103 mg, 0.74 mmol, 1.5 eq) in 0.5 mL of dry dimethylformamide (DMF). Ethyl iodide (115 mg, 0.74 mmol) was then added, the vial was capped, and the slurry heated to 50° C. with vigorous stirring overnight. The slurry was diluted with 20 mL water and extracted into 15 mL of dichloromethane. The organic layer was then washed with 20 mL portions of saturated NaHCO3, water, and brine; then dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in a few mL of dichloromethane and purified by radial chromatography, eluting using hexanes, then 4:1 hexanes:EtOAc, to provide 135 mg (63%) of the title compound as pinkish-white crystals.

Workup

  1. customIn a 4 mL screw cap vial
  2. customfitted with a small egg-shaped stir bar
  3. customthe vial was capped
  4. extractionextracted into 15 mL of dichloromethane
  5. washThe organic layer was then washed with 20 mL portions of saturated NaHCO3, water, and brine
  6. dry with materialthen dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in a few mL of dichloromethane
  9. custompurified by radial chromatography
  10. washeluting

Sources & evidence

ORD record
ord-eb8c5ca016bf4ce7a4ffaba58c696d5b
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

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