Iodine → HCID 67517493, compound

HRID 1508536Notes

Reaction equation

HRID 1508536 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[C:11]([CH3:20])=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=1.[I:21]I>S([O-])([O-])(=O)=O.[Ag+2].CO>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:21])=[CH:4][C:3]=1[C:10]1[C:11]([CH3:20])=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 807IodineHCID 67514197HCID 67514197, compound

Product 1

HCID 67517493HCID 67517493, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

Methyl 5-(2-fluoro-4-methoxyphenyl)-4-methylpyridine-2-carboxylate (190 mg, 0.690 mmol), silver sulfate (430 mg, 1.380 mmol), iodine (0.071 ml, 1.380 mmol) and MeOH (10 mL) were stirred at room temperature overnight. The crude mixture was filtered. The filtrate was concentrated in vacuo. The resulting pot residue was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 50 g cartridge). The column was eluted by an EtOAc/hexane mixture (0% to 40%). Related fractions were pooled and evaporated to afford a colorless oil as the titled compound. LCMS calc.=400.99. found=402.08 (M+H)+.

Workup

  1. filtrationThe crude mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe resulting pot residue was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 50 g cartridge)
  4. washThe column was eluted by an EtOAc/hexane mixture (0% to 40%)
  5. customevaporated

Sources & evidence

ORD record
ord-2aa25e3c387547c3a2b7c083fc2bba9f
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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