8-(4-{[tert-Butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloro-N-methoxy-N-methylquinoline-7-carboxamide → 1-[8-(4-{[tert-Butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethanone
Reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]([C:26](N(OC)C)=[O:27])=[CH:17][C:18]([Cl:25])=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:32][Mg]Br>O1CCCC1>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[C:16]([C:26](=[O:27])[CH3:32])=[CH:17][C:18]([Cl:25])=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 8-(4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloro-N-methoxy-N-methylquinoline-7-carboxamide (312 mg, 0.672 mmol) in tetrahydrofuran (0.9 mL) was added 1.4 M methylmagnesium bromide in tetrahydrofuran (2.9 mL, 4.0 mmol). The reaction was stirred at room temperature overnight, then quenched with sat. ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and then concentrated to dryness under reduced pressure to afford the desired product (0.275 g, 98%). LCMS calculated for C22H32ClN2O2Si (M+H)+: m/z=419.2; Found: 419.1.
Workup
- customquenched with sat. ammonium chloride
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-6584d79d0f5b4ac3a809851f64d87a56
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680108B2
Reaction notes
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