Iodine → HCID 89522279, compound

HRID 540455Notes

Reaction equation

HRID 540455 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-34e88ce5a5734958a17bc8bcb19374a9
Source dataset
uspto-grants-2014_10
Patent number
US08871738B2

Reaction notes

Loading…