Water → 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2-methoxy-5-methylpyridine

HRID 1912268Notes

Reaction equation

HRID 1912268 reaction equation
[CH3:1][Zn]C.[CH3:4][O:5][C:6]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[C:23]([CH3:31])[C:7]=1[C:8]([C:10]1[C:11]([O:21][CH3:22])=[N:12][CH:13]=[C:14](Br)[C:15]=1[C:16]([F:19])([F:18])[F:17])=[O:9].O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:4][O:5][C:6]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[C:23]([CH3:31])[C:7]=1[C:8]([C:10]1[C:11]([O:21][CH3:22])=[N:12][CH:13]=[C:14]([CH3:1])[C:15]=1[C:16]([F:19])([F:18])[F:17])=[O:9]

Participants

6

Reactant 3

HCID 962WaterHCID 230826073-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-bromo-4-trifluoromethyl-2-methoxypyridineHCID 178477796HCID 178477796, compound

Product 1

HCID 230825983-(2,3,4-Trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2-methoxy-5-methylpyridineYield 97.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.80 ml (3.80 mmol) of dimethylzinc (1.0 mol/l hexane solution) was dropwise added at 0° C. to a solution having 0.60 g (1.29 mmol) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-trifluoromethyl-2-methoxypyridine obtained in Step (d) and 0.10 g (0.09 mmol) of tetrakis(triphenylphosphine)palladium dissolved in 10 ml of tetrahydrofuran, and the temperature was increased naturally, followed by stirring at room temperature for 8 days. Water was added to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. After extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 0.50 g (yield: 96%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2-methoxy-5-methylpyridine.

Workup

  1. temperaturethe temperature was increased naturally
  2. customto terminate
  3. customthe reaction, and tetrahydrofuran
  4. distillationwas distilled off under reduced pressure
  5. extractionAfter extraction with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6a72e3f4c01b4bf3b022f82bb9855cb0
Source dataset
uspto-grants-2013_12
Patent number
US08609150B2

Reaction notes

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