Tetrabutylammonium Fluoride → methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylate
Reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:8]([C:21]2[CH:25]=[CH:24][N:23]([Si](C(C)C)(C(C)C)C(C)C)[CH:22]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:8]([C:21]2[CH:25]=[CH:24][NH:23][CH:22]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-[1-[tris(propan-2-yl)silyl]-1H-pyrrol-3-yl]quinoxaline-6-carboxylate (150 mg, 0.30 mmol) in tetrahydrofuran (30 ml) was added Tetra-n-butylammonium fluoride (TBAF) (80 mg, 0.31 mmol) with stirring for 10 min at room temperature. The reaction was then quenched with water (10 ml). The resulting solution was extracted with dichloromethane (3×10 ml) and the organic layers combined and dried over anhydrous magnesium sulfate, concentrated under vacuum to afford methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylate as a light yellow solid (100 mg, 98%).
Workup
- customThe reaction was then quenched with water (10 ml)
- extractionThe resulting solution was extracted with dichloromethane (3×10 ml)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-e5e98a2862b44472a4e42c5e9dafb58d
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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