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

HRID 1943653Notes

Reaction equation

HRID 1943653 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:28]=[CH:27][CH:26]=[CH:25][CH:24]=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.O>ClCCl>[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]=[CH: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 3

HCID 962WaterHCID 25134Boron tribromideHCID 66936674(3,5-Dibromo-4-methoxy-phenyl)-(7-phenyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

Product 1

HCID 44608066(3,5-Dibromo-4-hydroxy-phenyl)-(7-phenyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanoneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 5 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(7-phenyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone (14 mg, 0.03 mmol) was dissolved in dichloromethane and then cooled to 0□. 1.0M Boron tribromide dissolved in dichloromethane (0.17 ml, 0.17 mmol) was added and then stirred at 0□ for 15 hours. After completion of the reaction, water was added thereto and the mixture was extracted with ethyl acetate and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=40:1. The fractions containing the product were collected and evaporated to obtain the target compound 20 as white solid (8.7 mg, 64%).

Workup

  1. temperaturecooled to 0□
  2. additionwas added
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  9. additionThe fractions containing the product
  10. customwere collected
  11. customevaporated

Sources & evidence

ORD record
ord-d0d5cf0ea1784937973eb75cdcd4f0f4
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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