Pyridine → Methyl 3-(benzyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

HRID 1403531Notes

Reaction equation

HRID 1403531 reaction equation
[CH2:1]([N:8]([CH3:24])[C:9]1[C:10](=[O:23])[NH:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[O:31](S(C(F)(F)F)(=O)=O)[S:32]([C:35]([F:38])([F:37])[F:36])(=O)=[O:33]>ClCCl>[CH2:1]([N:8]([CH3:24])[C:9]1[C:10]([O:23][S:32]([C:35]([F:38])([F:37])[F:36])(=[O:33])=[O:31])=[N:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70664852Methyl 3-(benzyl(methyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 86670574Methyl 3-(benzyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-[benzyl(methyl)amino]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (200 mg, 0.62 mmol) in dichloromethane (30 mL) was added pyridine (196 mg, 2.48 mmol), followed by Tf2O (349 mg, 1.24 mmol) at room temperature. The mixture was stirred overnight at room temperature, then quenched with water (100 mL), extracted with dichloromethane (3×20 mL1), and the organic layers combined and dried over anhydrous magnesium sulfate and concentrated under vacuum to afford methyl 3-(benzyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as a red solid (300 mg, crude).

Workup

  1. customquenched with water (100 mL)
  2. extractionextracted with dichloromethane (3×20 mL1)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5af72163f0a5453da8e3906ce22c5dd9
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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