Water → HCID 69137025, compound

HRID 512461Notes

Reaction equation

HRID 512461 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[NH:11]1.O>C(O)(=O)C>[Br:1][C:13]1[CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:10](=[O:9])[NH:11][C:12]=1[C:20]([F:21])([F:23])[F:22]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 15217844Methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 69137025HCID 69137025, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At room temperature, 0.36 g (2.04 mmol) of N-bromosuccinimide was added to a suspension of 0.3 g (1.36 mmol) of methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate in 10 ml of glacial acetic acid, and the mixture was then heated under reflux for 2 days. The reaction mixture was then added to water and extracted with dichloromethane. The extract was concentrated, and the residue was purified further by preparative HPLC. This gave 227 mg (56% of theory) of a colorless powder.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for 2 days
  3. extractionextracted with dichloromethane
  4. concentrationThe extract was concentrated
  5. customthe residue was purified further by preparative HPLC

Sources & evidence

ORD record
ord-26fc9d545ea24eeb9ac5de8240115e04
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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