(S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate → Tert-butyl 1-(6-fluoro-4-(3-methylpyridin-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N:12]=1)=O.O=[C:19]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[C@@H:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:21]>CC(O)C.O.O.[Na+].Cl[Au-](Cl)(Cl)Cl>[F:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:19]([CH:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[CH3:26])[CH3:21])[C:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)=[C:9]2[C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N:12]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of (2-amino-5-fluorophenyl)(3-methylpyridin-2-yl)methanone (0.29 g, 1.26 mmol), (S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate (0.366 g, 1.386 mmol), and sodium tetrachloroaurate(iii) dihydrate (0.025 g, 0.063 mmol) in 2-propanol (5.0 mL) was stirred at 80° C. for 24 h under an argon atmosphere, then at room temperature for an additional 48 h. The solution was purified by silica gel column chromatography eluting with a gradient of 10-40% EtOAc in hexane to afford tert-butyl 1-(6-fluoro-4-(3-methylpyridin-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate as a dark solid: LC-MS (ESI) m/z 459.2 [M+H]+.
Workup
- customThe solution was purified by silica gel column chromatography
- washeluting with a gradient of 10-40% EtOAc in hexane
Sources & evidence
- ORD record
- ord-1f1e2d5cffe2438a81af4ee358475eae
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765768B2
Reaction notes
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