N-bromobutanimide → 2-Bromo-1-(6-bromoquinoxalin-2-yl)ethanone

HRID 625609Notes

Reaction equation

HRID 625609 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([O:22]CC)=[CH2:21])[CH:14]=[N:13]2>C1COCC1.O.CO>[Br:8][CH2:22][C:20]([C:15]1[CH:14]=[N:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10]([Br:9])[CH:11]=2)[N:16]=1)=[O:21]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 584987636-Bromo-2-(1-ethoxyvinyl)quinoxaline

Product 1

HCID 584986562-Bromo-1-(6-bromoquinoxalin-2-yl)ethanoneYield 59%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NBS (55.1 mg, 0.310 mmol) was added to a solution of 6-bromo-2-(1-ethoxyvinyl)quinoxaline (72 mg, 0.26 mmol) in THF (2 mL) and water (0.500 mL) and the mixture was stirred at rt for 2 h. The reaction was diluted with MeOH and purified by prep HPLC (H2O-MeOH with 10 mM NH4OAc buffer) to yield 2-bromo-1-(6-bromoquinoxalin-2-yl)ethanone (50 mg, 0.15 mmol, 59% yield) as white solid. LC-MS retention time 2.40 min; m/z 329 [M+H]+. (Column PHENOMENEX® Luna 3.0×50 mm S10. Solvent A=90% water: 10% methanol: 0.1% TFA. Solvent B=10% water: 90% methanol: 0.1% TFA. Flow Rate=4 mL/min. Start % B=0. Final % B=100. Gradient Time=3 min. Wavelength=220).

Workup

  1. custompurified by prep HPLC (H2O-MeOH with 10 mM NH4OAc buffer)

Sources & evidence

ORD record
ord-c7144936cf744eb185748e1746d24d20
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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