Sodium hydride → 4-[2-(3,5-dibromo-4-hydroxy-phenyl)-2-oxo-ethyl]-4H-pyrido[4,3-b][1,4]oxazin-3-one
Reaction equation
[O:1]1[CH2:6][C:5](=[O:7])[NH:4][C:3]2[CH:8]=[N:9][CH:10]=[CH:11][C:2]1=2.[H-].[Na+].Br[CH2:15][C:16]([C:18]1[CH:23]=[C:22]([Br:24])[C:21]([OH:25])=[C:20]([Br:26])[CH:19]=1)=[O:17]>CN(C)C=O>[Br:24][C:22]1[CH:23]=[C:18]([C:16](=[O:17])[CH2:15][N:4]2[C:5](=[O:7])[CH2:6][O:1][C:2]3[CH:11]=[CH:10][N:9]=[CH:8][C:3]2=3)[CH:19]=[C:20]([Br:26])[C:21]=1[OH:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 10 ml flask, 4H-pyrido[4,3-b][1,4]oxazin-3-one (50 mg, 0.33 mmol) was dissolved in N,N-dimethyl formamide (2.0 ml) and then cooled to 0□. Sodium hydride (15 mg, 0.37 mmol) was added thereto at 0□ and then stirred at room temperature for 30 minutes. The reaction mixture was cooled to 0□, 2-bromo-1-(3,5-dibromo-4-hydroxy-phenyl)-ethanone (124 mg, 0.33 mmol) was added thereto dropwise and stirred at 0□ for 30 minutes, and then the mixture was stirred at room temperature for 1 hour. The precipitates formed were filtered and washed with acetonitrile. The resulting solid was recrystallized from methanol to obtain the target compound 56, i.e., 4-[2-(3,5-dibromo-4-hydroxy-phenyl)-2-oxo-ethyl]-4H-pyrido[4,3-b][1,4]oxazin-3-one, as white solid (48 mg, 33%).
Workup
- temperaturecooled to 0□
- additionwas added
- stirringdropwise and stirred at 0□ for 30 minutes
- stirringthe mixture was stirred at room temperature for 1 hour
- customThe precipitates formed
- filtrationwere filtered
- washwashed with acetonitrile
- customThe resulting solid was recrystallized from methanol
Sources & evidence
- ORD record
- ord-a4fb187adafc400e8122324df24ff487
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394792B2
Reaction notes
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