Dimethylformamide → 4-(2,3,4-Trimethoxy-6-methylbenzoyl)-2bromo-3-chloro-5-methoxypyridine

HRID 1835428Notes

Reaction equation

HRID 1835428 reaction equation
CN(C)C=O.P(Br)(Br)([Br:8])=O.[CH3:11][O:12][C:13]1[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[C:27]([CH3:35])[C:14]=1[C:15]([C:17]1[C:22]([O:23][CH3:24])=[CH:21][N+:20]([O-])=[CH:19][C:18]=1[Cl:26])=[O:16]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[C:27]([CH3:35])[C:14]=1[C:15]([C:17]1[C:22]([O:23][CH3:24])=[CH:21][N:20]=[C:19]([Br:8])[C:18]=1[Cl:26])=[O:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24613Phosphorus oxybromideHCID 235035884-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine-N-oxide

Product 1

HCID 235035924-(2,3,4-Trimethoxy-6-methylbenzoyl)-2bromo-3-chloro-5-methoxypyridineYield 743%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 ml of dimethylformamide was added to 2.5 ml of toluene, the mixture was cooled with ice, and 0.7 g (0.2 mmol) of phosphorus oxybromide was dropwise added thereto. After the mixture was stirred under cooling with ice for 10 minutes, 0.42 g (0.1 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine-N-oxide obtained in Synthesis Example 14 (a) was added thereto. After the mixture was stirred under cooling with ice for 30 minutes, the temperature was recovered to room temperature, followed by stirring for 2 hours. 10 ml of water was added to the mixture to terminate the reaction, and ethyl acetate was added thereto for extraction. The organic layer was dried over anhydrous sodium sulfate, subjected to filtration and purified by silica gel column chromatography to obtain 0.32 g (yield 65%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2bromo-3-chloro-5-methoxypyridine (compound No. 245; m.p. 97-99° C.).

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice for 10 minutes
  3. additionwas added
  4. stirringAfter the mixture was stirred
  5. temperatureunder cooling with ice for 30 minutes
  6. customthe temperature was recovered to room temperature
  7. stirringby stirring for 2 hours
  8. addition10 ml of water was added to the mixture
  9. customto terminate
  10. customthe reaction, and ethyl acetate
  11. additionwas added
  12. extractionfor extraction
  13. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  14. filtrationsubjected to filtration
  15. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b57ebd57daed4eb2bb4b1fe154ce55e9
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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