Sodium Carbonate → 2-(5-Bromo-2-fluoropyridin-3-yl)pyrimidine
Reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:14][C:15]1[CH:16]=[C:17](B(O)O)[C:18]([F:21])=[N:19][CH:20]=1>O1CCOCC1>[Br:14][C:15]1[CH:16]=[C:17]([C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[C:18]([F:21])=[N:19][CH:20]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
2-Bromopyrimidine (5.42 g, 34.1 mmol), sodium carbonate (22.75 mL, 45.5 mmol), 5-bromo-2-fluoropyridine-3-boronic acid (5 g, 22.75 mmol, commercially available from Frontier Scientific, Inc., Logan Utah), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium(II) (1.858 g, 2.275 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) were combined in dioxane (32.5 mL) and stirred at 100° C. overnight. LC-MS indicated good conversion to desired product. The material thus obtained was absorbed 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 10% MeOH in DCM, to provide 2-(5-bromo-2-fluoropyridin-3-yl)pyrimidine (4.37 g, 17.20 mmol, 76% yield) as yellow solid. m/z (ESI) 253.8.
Sources & evidence
- ORD record
- ord-fbe74480eefa424f9615a3e935fd9dde
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340549B2
Reaction notes
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