Potassium Carbonate → 1-(3,5-Dibromo-4-hydroxy-phenyl)-2-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-ethanone

HRID 1943710Notes

Reaction equation

HRID 1943710 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2.Br[CH2:12][C:13]([C:15]1[CH:20]=[C:19]([Br:21])[C:18]([OH:22])=[C:17]([Br:23])[CH:16]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:21][C:19]1[CH:20]=[C:15]([C:13](=[O:14])[CH2:12][N:4]2[CH2:5][CH2:6][O:1][C:2]3[CH:10]=[CH:9][N:8]=[CH:7][C:3]2=3)[CH:16]=[C:17]([Br:23])[C:18]=1[OH:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 37844242-Bromo-1-(3,5-dibromo-4-hydroxyphenyl)ethanoneHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 446085431-(3,5-Dibromo-4-hydroxy-phenyl)-2-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-ethanoneYield 58.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 10 ml flask, (3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (60 mg, 0.44 mmol) was dissolved in anhydrous acetonitrile (5 ml). At room temperature, 2-bromo-1-(3,5-dibromo-4-hydroxy-phenyl)-ethanone (164 mg, 0.44 mmol) and potassium carbonate (121 mg, 0.88 mmol) were added thereto and then stirred at room temperature for 16 hours. The reaction mixture was filtered and the resulting white solid was recrystallized from methanol to obtain the target compound 54 as white solid (110 mg, 58.5%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe resulting white solid was recrystallized from methanol

Sources & evidence

ORD record
ord-58d75cc9259843fbb641ef09590e0b6f
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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