Pyridine → Methyl 3-(isopropyl(methyl)amino)-7-methoxy-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate
Reaction equation
[CH:1]([N:4]([CH3:22])[C:5]1[C:6](=[O:21])[NH:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([O:19][CH3:20])[CH:9]=2)([CH3:3])[CH3:2].N1C=CC=CC=1.[O:29](S(C(F)(F)F)(=O)=O)[S:30]([C:33]([F:36])([F:35])[F:34])(=O)=[O:31]>ClCCl>[CH:1]([N:4]([CH3:22])[C:5]1[C:6]([O:21][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:31])=[O:29])=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([O:19][CH3:20])[CH:9]=2)([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 3-(isopropyl(methyl)amino)-7-methoxy-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (2.0 g, 6.55 mmol) in dichloromethane (80 mL) was added Pyridine (2.0 g, 25.28 mmol) and Tf2O (3.66 g, 12.97 mmol) with stirring overnight under an atmosphere of nitrogen at room temperature. The reaction mixture was then quenched with water (50 mL) and extracted with dichloromethane (3×80 mL). The organic layers were combined and dried over anhydrous magnesium sulfate and concentrated in vacuo to afford methyl 3-(isopropyl(methyl)amino)-7-methoxy-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as red oil (2.50 g, crude), which was used in the next step directly.
Workup
- customThe reaction mixture was then quenched with water (50 mL)
- extractionextracted with dichloromethane (3×80 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-00f83768bf0a4ea095931896dfc94b7b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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