methyl 2-(1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate → methyl 3-(isopropyl(methyl)amino)-2-(5-methoxy-1H-indol-2-yl)quinoxaline-6-carboxylate
Reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:19]1[C:28]([N:29]([CH:31]([CH3:33])[CH3:32])[CH3:30])=[N:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:34]([O:36][CH3:37])=[O:35])[CH:25]=2)[N:20]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:31]([N:29]([CH3:30])[C:28]1[C:19]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)=[N:20][C:21]2[C:26]([N:27]=1)=[CH:25][C:24]([C:34]([O:36][CH3:37])=[O:35])=[CH:23][CH:22]=2)([CH3:32])[CH3:33]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methyl 2-(1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (180.0 mg, 0.36 mmol) in 20% TFA/DCM (30 mL) was stirred overnight at room temperature and then quenched by the addition of water (100 ml). The reaction mixture was adjusted to pH 7 with aq. sodium bicarbonate, extracted with chloroform, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column with 0.1%-1% methanol in dichloromethane to afford methyl 3-(isopropyl(methyl)amino)-2-(5-methoxy-1H-indol-2-yl)quinoxaline-6-carboxylate as a light yellow solid (100.0 mg, 69%).
Workup
- customquenched by the addition of water (100 ml)
- extractionextracted with chloroform
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by a silica gel column with 0.1%-1% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-7ec75c1817bd478697420c22d49ca591
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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