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

HRID 1943723Notes

Reaction equation

HRID 1943723 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[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH:26]=[N: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.[OH-].[Na+]>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[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH:26]=[N:25][CH:24]=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 14798Sodium HydroxideHCID 25134Boron tribromideHCID 66936506(3,5-Dibromo-4-methoxy-phenyl)-(7-isoquinolin-4-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

Product 1

HCID 44608709(3,5-Dibromo-4-hydroxy-phenyl)-(7-isoquinolin-4-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanoneYield 27.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere, in a 10 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(7-isoquinolin-4-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone (11.3 mg, 0.020 mmol) was dissolved in dichloromethane, and then cooled to 0□. 1.0M Boron tribromide dissolved in dichloromethane (0.2 ml, 0.203 mmol) was added thereto and then stirred at room temperature for 18 hours. After adjusting to pH 6 with 1N NaOH solution, the mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. Diethyl ether was added to the formed solid and stirred for 30 minutes and then filtered to obtain the target compound 61 as white solid (3.0 mg, 27%).

Workup

  1. temperaturecooled to 0□
  2. additionwas added
  3. extractionthe 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. additionDiethyl ether was added to the formed solid
  8. stirringstirred for 30 minutes
  9. filtrationfiltered

Sources & evidence

ORD record
ord-c0af605cf05c43fe9334219fcb3e5b39
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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