Sodium Hydroxide → HCID 44610279, compound

HRID 1943642Notes

Reaction equation

HRID 1943642 reaction equation
[CH:1]1([C:4]2[CH:25]=[N:24][C:7]3[O:8][CH2:9][CH2:10][N:11]([C:12]([C:14]4[CH:19]=[C:18]([Br:20])[C:17]([O:21]C)=[C:16]([Br:23])[CH:15]=4)=[O:13])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[CH:1]1([C:4]2[CH:25]=[N:24][C:7]3[O:8][CH2:9][CH2:10][N:11]([C:12]([C:14]4[CH:15]=[C:16]([Br:23])[C:17]([OH:21])=[C:18]([Br:20])[CH:19]=4)=[O:13])[C:6]=3[CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 66936878HCID 66936878, compound

Product 1

HCID 44610279HCID 44610279, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 10 ml flask, (7-cyclopropyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-(3,5-dibromo-4-methoxy-phenyl)-methanone (9.0 mg, 0.019 mmol) was dissolved in dichloromethane, and then cooled to 0□. 1.0M Boron tribromide dissolved in dichloromethane (0.2 ml*2, 0.203 mmol) was added thereto and then stirred at room temperature for 16 hours. The pH was adjusted to 6 with 1N sodium hydroxide solution and the reaction mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure to obtain solid. The resulting solid was recrystallized from dichloromethane to obtain white solid (6.7 mg, 84%).

Workup

  1. temperaturecooled to 0□
  2. additionwas added
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto obtain solid
  8. customThe resulting solid was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-bd4b0053330040b1a4274ded94e74976
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

Loading…