Boron tribromide → HCID 44610276, compound

HRID 1943635Notes

Reaction equation

HRID 1943635 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[CH:19]=[N:20][CH:21]=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[O:8]C.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[N:20][CH:21]=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[OH:8]

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 44610275HCID 44610275, compound

Product 1

HCID 44610276HCID 44610276, compound

Procedure

By the same method as in Example 3, (3,5-dibromo-4-methoxy-phenyl)-(2,3-dihydro-pyrido[3,4-b][1,4]oxazin-1-yl)-methanone (60 mg, 0.140 mmol) and 1M solution of boron tribromide (0.84 ml, 0.840 mmol) were reacted, and then the reaction mixture was neutralized (pH=7) by using saturated solution of sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure to obtain solid. The obtained solid was recrystallized from dichloromethane and n-hexane to obtain the target compound 6, (3,5-dibromo-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[3,4-b][1,4]oxazin-1-yl)-methanone, as white solid (28 mg, 48%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto obtain solid
  6. customThe obtained solid was recrystallized from dichloromethane and n-hexane

Sources & evidence

ORD record
ord-d4da8b8b7abf44c5b258e25e617f177e
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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