Iodine → HCID 89522279, compound

HRID 529713Notes

Reaction equation

HRID 529713 reaction equation
[I:1]I.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([CH3:21])=[CH:13][C:14]([C:17]([O:19][CH3:20])=[O:18])=[N:15][CH:16]=2)=[CH:7][CH:6]=1>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:6]1[CH:7]=[C:8]([C:11]2[C:12]([CH3:21])=[CH:13][C:14]([C:17]([O:19][CH3:20])=[O:18])=[N:15][CH:16]=2)[CH:9]=[CH:10][C:5]=1[O:4][CH3:3]

Participants

5

Reactant 2

HCID 807Iodine2×HCID 86682279HCID 86682279, compound

Product 1

HCID 89522279HCID 89522279, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

A suspension of iodine (2.45 g, 9.66 mmol), silver sulfate (3.01 g, 9.66 mmol) and methyl 5-(4-methoxyphenyl)-4-methylpyridine-2-carboxylate (2.47 g, 9.59 mmol) in MeOH (20 mL) was stirred at room temperature for 3.5 hours. It was then heated at 36° C. for 4 hours and then at room temperature for another 16 hours. Additional iodine (0.8 g, 3.15 mmol) and silver sulfate (1 g, 3.2 mmol) were added and the reaction was heated to 36° C. for 3 hours. The volatiles were removed and the reaction was diluted with ethyl acetate and aqueous sodium thiosulfate. The organic was washed with brine, dried over sodium sulfate, filtered and then concentrated. The resultant oil was purified by column chromatography to yield methyl 5-(3-iodo-4-methoxyphenyl)-4-methylpyridine-2-carboxylate (2.35 g, 6.12 mmol) as a white solid. MS ESI calc'd. for C15H15INO3 [M+H]+ 384.0, found 384.0.

Workup

  1. temperatureIt was then heated at 36° C. for 4 hours
  2. waitat room temperature for another 16 hours
  3. temperaturethe reaction was heated to 36° C. for 3 hours
  4. customThe volatiles were removed
  5. additionthe reaction was diluted with ethyl acetate and aqueous sodium thiosulfate
  6. washThe organic was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resultant oil was purified by column chromatography

Sources & evidence

ORD record
ord-37313e4c969846f79413dfff8b289e52
Source dataset
uspto-grants-2016_05
Patent number
US09346825B2

Reaction notes

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