Pyridine → (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[C:9](=[O:13])[NH:10]2)=[CH:5][C:4]=1[C:20]([O:22][CH3:23])=[O:21].N1C=CC=CC=1.[O:30](S(C(F)(F)F)(=O)=O)[S:31]([C:34]([F:37])([F:36])[F:35])(=O)=[O:32]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[C:9]([O:13][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:30])=[N:10]2)=[CH:5][C:4]=1[C:20]([O:22][CH3:23])=[O:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (1.0 g, 3.15 mmol) in dichloromethane (80 ml) was added pyridine (990 mg, 12.52 mmol) and Tf2O (1.69 g, 5.99 mmol), and the reaction was stirred overnight under an atmosphere of nitrogen at room temperature. The reaction mixture was then quenched with water (200 ml), extracted with dichloromethane (3×30 mL), the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as red oil (1.20 g, crude), which was used in the next step directly.
Workup
- customThe reaction mixture was then quenched with water (200 ml)
- extractionextracted with dichloromethane (3×30 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-05e187199bce40d19712e50bcda0dd6b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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