Methanol → HCID 44608071, compound

HRID 1943672Notes

Reaction equation

HRID 1943672 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]([C:12]([C:14]3[CH:19]=[C:18]([Br:20])[C:17]([O:21]C)=[C:16]([Br:23])[CH:15]=3)=[O:13])[CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][N:3]=1.B(Br)(Br)Br.ClCCl.CO>ClC(Cl)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:11]2[N:10]([C:12]([C:14]3[CH:15]=[C:16]([Br:23])[C:17]([OH:21])=[C:18]([Br:20])[CH:19]=3)=[O:13])[CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 25134Boron tribromideHCID 86650559HCID 86650559, compound

Product 1

HCID 44608071HCID 44608071, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 63651,1-DichloroethaneSolvent

Procedure

In a 5 ml flask equipped with a reflux apparatus, (5-chloro-2,3-dihydro -pyrido[4,3-b][1,4]oxazin-4-yl)-(3,5-dibromo-4-methoxy-phenyl)-methanone (48 mg, 0.1 mmol) was dissolved in dichloroethane (0.5 ml) and chloroform (0.5 ml). 1.0M Boron tribromide dissolved in dichloromethane (1 ml, 1 mmol) was added thereto dropwise at room temperature. The reaction mixture was stirred at 450 for 18 hours. After cooling to room temperature, methanol (1 ml) was added and then stirred at room temperature for 10 minutes. After evaporating under reduced pressure, dichloromethane was added and then stirred. The reaction mixture was filtered to obtain the target compound 30 as white solid (24 mg, 54%).

Workup

  1. additionwas added
  2. customdropwise at room temperature
  3. stirringstirred at room temperature for 10 minutes
  4. customAfter evaporating under reduced pressure, dichloromethane
  5. additionwas added
  6. stirringstirred
  7. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-77a1dfff7d904ed8bca5f42ada668eb0
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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