Sodium Carbonate → (S)-3-(4-(6-Fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one
Reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]([CH3:20])([CH3:19])[O:10][C:9]2=[O:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:28][C:29]1[C:34]([C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1>O1CCOCC1>[F:28][C:29]1[N:30]=[CH:31][C:32]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[C@@H:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:11]([CH3:20])([CH3:19])[O:10][C:9]3=[O:21])=[CH:4][CH:3]=2)=[CH:33][C:34]=1[C:35]1[N:36]=[CH:37][CH:38]=[CH:39][N:40]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
(S)-3-(4-Iodophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (Intermediate C)(2.61 g, 6.64 mmol), sodium carbonate (6.64 mL, 13.28 mmol), 2-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrimidine (Intermediate H) (2 g, 6.64 mmol), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium(II) (0.542 g, 0.664 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) were combined in dioxane (16.60 mL) and stirred at 110° C. overngight. LC-MS indicated that there was complete conversion to the desired product. The final reaction material was adsorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide (S)-3-(4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one as yellow solid. m/z (ESI) 441.3 (M+H)+.
Sources & evidence
- ORD record
- ord-1c84c7fd5f834c58a727ed7543decce9
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340549B2
Reaction notes
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