(2,3,4-Trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol → 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-fluoro-4-iodo-5-methylpyridine

HRID 1912255Notes

Reaction equation

HRID 1912255 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]([C:16]1[C:17]([F:24])=[N:18][CH:19]=[C:20]([CH3:23])[C:21]=1[I:22])[OH:15]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[C:14]([C:16]1[C:17]([F:24])=[N:18][CH:19]=[C:20]([CH3:23])[C:21]=1[I:22])=[O:15]

Participants

4

Reactant 1

HCID 23082609(2,3,4-Trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol

Product 1

HCID 230825813-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-fluoro-4-iodo-5-methylpyridineYield 65%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

17.3 g (0.18 mol) of manganese dioxide was added to a solution having 4.35 g (9.70 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol obtained in Step (b) dissolved in 130 ml of toluene, followed by reflux with heating for 2 hours. After cooling to room temperature, manganese dioxide was removed by filtration on the pad of celite, and toluene was distilled off under reduced pressure, followed by purification by silica gel chromatography to obtain 2.80 g (yield: 65%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4-iodo-5-methylpyridine (Compound No. 18, melting point 140 to 141° C.).

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 2 hours
  3. custommanganese dioxide was removed by filtration on the pad of celite, and toluene
  4. distillationwas distilled off under reduced pressure
  5. customfollowed by purification by silica gel chromatography

Sources & evidence

ORD record
ord-0399b005a9f842bb83c3947a69fc4969
Source dataset
uspto-grants-2013_12
Patent number
US08609150B2

Reaction notes

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