Potassium Carbonate → 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-fluoro-4,5-dimethylpyridine

HRID 1912256Notes

Reaction equation

HRID 1912256 reaction equation
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([CH3:24])[C:4]=1[C:5]([C:7]1[C:8]([F:15])=[N:9][CH:10]=[C:11]([CH3:14])[C:12]=1I)=[O:6].[C:25](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>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.O1CCOCC1>[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([CH3:24])[C:4]=1[C:5]([C:7]1[C:8]([F:15])=[N:9][CH:10]=[C:11]([CH3:14])[C:12]=1[CH3:25])=[O:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 230825813-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-fluoro-4-iodo-5-methylpyridine

Product 1

HCID 230825853-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-fluoro-4,5-dimethylpyridineYield 70.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

1.50 g (3.37 mmol) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4-iodo-5-methylpyridine obtained in Step (c), 1.40 g (10.1 mmol) of potassium carbonate, 0.39 g (0.34 mmol) of tetrakis(triphenylphosphine)palladium, 15 ml of dioxane and 0.42 g (1.67 mmol) of 50% trimethylboroxin were mixed, followed by reflux with heating for 6 hours. After cooling to room temperature, filtration on the pad of celite and washing with ethyl acetate and tetrahydrofuran were carried out, the solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel chromatography to obtain 0.79 g (yield: 70%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4,5-dimethylpyridine (Compound No. 19).

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 6 hours
  3. filtrationfiltration on the pad of celite
  4. washwashing with ethyl acetate and tetrahydrofuran
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe obtained crude product
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-bb90fead01f549ddaa6bd00a2ab39007
Source dataset
uspto-grants-2013_12
Patent number
US08609150B2

Reaction notes

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