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 1943706ノート

反応式

HRID 1943706 の反応式
[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]

参加物

5

反応物 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

生成物 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]-methanone収率 53.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8058Hexane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-43a534b2d02a435ba420e2c2df861f5f
出典データセット
uspto-grants-2013_03
特許番号
US08394792B2

反応ノート

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