Cesium carbonate → N-ethyl-N'-(6-fluoro-3,4'-bipyridin-2'-yl)urea
Reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:12]([NH:11][C:9]([NH:8][C:4]1[CH:3]=[C:2]([C:18]2[CH:17]=[N:16][C:15]([F:14])=[CH:20][CH:19]=2)[CH:7]=[CH:6][N:5]=1)=[O:10])[CH3:13]Participants
Procedure
N-(4-bromopyridin-2-yl)-N′-ethylurea (Intermediate 33, 0.40 g, 1.64 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.057 g, 4.92 mmol), tetrakis triphenyl phosphine palladium (0.189 g, 0.16 mmol), and cesium carbonate (1.16 g, 4.92 mmol) were taken in a microwave vial and degassed with nitrogen. A dioxane:water (4:1, 10 mL) solution was added to the vial and the mixture was microwaved at 110° C. for half an hour. The palladium was filtered off, and the reaction was partitioned between water and ethyl acetate. The layers were separated, and the organic layer was washed with saturated sodium bicarbonate solution, water and brine, then dried over magnesium sulfate, and concentrated. The residue obtained was washed with acetonitrile to give the title compound as a white solid (360 mg).
Workup
- customdegassed with nitrogen
- additionA dioxane:water (4:1, 10 mL) solution was added to the vial and the mixture
- customwas microwaved at 110° C. for half an hour
- filtrationThe palladium was filtered off
- customthe reaction was partitioned between water and ethyl acetate
- customThe layers were separated
- washthe organic layer was washed with saturated sodium bicarbonate solution, water and brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue obtained
- washwas washed with acetonitrile
Sources & evidence
- ORD record
- ord-b8dfce097e2b42d2be4023ab6a3bd21c
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674801B2
Reaction notes
Loading…