Cesium fluoride → Methyl 3-(5-methylpyridin-2-yl)-5-(1,3-oxazol-2-yl)benzoate
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F-].[Cs+].C([Sn](CCCC)(CCCC)[C:26]1[O:27][CH:28]=[CH:29][N:30]=1)CCC.C(=O)(O)[O-].[Na+]>O1CCOCC1.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(OCC)(=O)C>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:4]([CH:3]=[C:2]([C:26]3[O:27][CH:28]=[CH:29][N:30]=3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:13][CH:14]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
To a degassed solution of methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate (1.0 g, 3.27 mmol) in 1,4-dioxane (20 mL) was added cesium fluoride (1.49 g, 9.80 mmol), 2-(tributylstannyl)-1,3-oxazole (2.34 g, 6.53 mmol) and Bis(tri-t-butylphosphine) palladium (83 mg, 0.163 mmol). The mixture was heated to 90° C. under nitrogen for 16 h, after which the reaction was cooled to 20° C. Ethyl acetate (200 mL) and saturated sodium bicarbonate solution (200 mL) were added. The organic layer was isolated and the aqueous layer was extracted with ethyl acetate (2×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was run through silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) to give the title compound (1 g). MS 295.1 (M+1).
Workup
- temperatureafter which the reaction was cooled to 20° C
- customThe organic layer was isolated
- extractionthe aqueous layer was extracted with ethyl acetate (2×)
- washThe combined organic extracts were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4da39b3d33c8442aa1ebd17169463b48
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461185B2
Reaction notes
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