Iodine → HCID 59325233, compound

HRID 2382155Notes

Reaction equation

HRID 2382155 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.II.FC(F)(F)C(OI([C:25]1[CH:30]=CC=C[CH:26]=1)OC(=O)C(F)(F)F)=O.[Cl:33]CCl>CO>[Cl:33][C:30]1[CH:25]=[CH:26][C:7]2[C:2](=[CH:3][C:4]([CH3:9])=[N:5][C:6]=2[CH3:8])[N:1]=1

Participants

6

Reactant 4

HCID 807IodineHCID 6344DichloromethaneHCID 770474-Amino-2,6-dimethylpyridineHCID 102317Bis(trifluoroacetoxy)iodobenzene

Product 1

HCID 59325233HCID 59325233, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Amino-2,6-dimethylpyridine (2.29 g, 18.7 mmol) was added to a solution of iodine (4.78 g, 18.8 mmol) and [bis(trifluoroacetoxy)iodo]benzene (8.1 g, 18.8 mmol) in dichloromethane (100 mL) and MeOH (30 mL). The mixture was stirred at room temperature for 16 hours. The reaction was quenched by addition of a mixture of saturated sodium metabisulphite solution (70 mL) and saturated sodium carbonate solution (300 mL). The organic phase was separated, washed with brine, and dried over sodium sulfate (Na2SO4). The solvent was removed and the product was purified by silica gel chromatography eluting with 30:1 dichloromethane:MeOH to afford the desired product (998 mg, 21.2%).

Workup

  1. customThe reaction was quenched by addition of a mixture of saturated sodium metabisulphite solution (70 mL) and saturated sodium carbonate solution (300 mL)
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. customThe solvent was removed
  6. customthe product was purified by silica gel chromatography
  7. washeluting with 30:1 dichloromethane

Sources & evidence

ORD record
ord-da4bf20602ed473c9cef7d6e6eb53f34
Source dataset
uspto-grants-2012_09
Patent number
US08258301B2

Reaction notes

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