Boron tribromide → (3,5-Dibromo-4-hydroxy-phenyl)-(7-pyridin-3-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl]-methanone

HRID 1943706Notes

Reaction equation

HRID 1943706 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[N:19]=[CH:20][C:21]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[O:8]C.B(Br)(Br)Br>ClCCl.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[N:19]=[CH:20][C:21]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 66936151(3,5-Dibromo-4-methoxy-phenyl)-(7-pyridin-3-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

Product 1

HCID 44608549(3,5-Dibromo-4-hydroxy-phenyl)-(7-pyridin-3-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl]-methanoneYield 53.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

In a 5 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(7-pyridin-3-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone (35 mg, 0.069 mmol) was dissolved in dichloromethane (1 ml), and the mixture was cooled to 0□. 1.0M Boron tribromide dissolved in dichloromethane (0.4 ml, 0.415 mmol) was added thereto and then stirred at room temperature for 15 hours. n-hexane solvent was added thereto and the formed solid was filtered. The resulting solid was dissolved in methanol and concentrated. After dissolving by adding water, the mixture was adjusted to pH 6 with saturated solution of sodium hydrogen carbonate, and extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was recrystallized from dichloromethane and n-hexane to obtain the target compound 52 as white solid (18 mg, 53%).

Workup

  1. temperaturethe mixture was cooled to 0□
  2. additionwas added
  3. filtrationthe formed solid was filtered
  4. dissolutionThe resulting solid was dissolved in methanol
  5. concentrationconcentrated
  6. dissolutionAfter dissolving
  7. additionby adding water
  8. extractionextracted with dichloromethane
  9. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customThe residue was recrystallized from dichloromethane and n-hexane

Sources & evidence

ORD record
ord-43a534b2d02a435ba420e2c2df861f5f
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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