1,3-Dibromobenzene → 4-(3-bromophenyl)-1-methyl-1H-pyrazole
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH3:9][N:10]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[N:11]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:8][C:4]1[CH:3]=[C:2]([C:13]2[CH:12]=[N:11][N:10]([CH3:9])[CH:14]=2)[CH:7]=[CH:6][CH:5]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
1,3-Dibromobenzene (0.38 mL, 3.2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (595 mg, 2.86 mmol), Pd(dppf)Cl2 (260 mg, 0.320 mmol), and potassium phosphate (2.0 g, 9.5 mmol) were combined in a flask and dissolved in dioxane (16.0 mL) and water (1.6 mL). The flask was then sealed and flushed with argon. The reaction mixture was allowed to stir at 90° C. for 90 minutes. The mixture was then cooled to ambient temperature and diluted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by MPLC on silica gel (50% EtOAc/hexanes) to afford the title compound.
Workup
- customThe flask was then sealed
- customflushed with argon
- temperatureThe mixture was then cooled to ambient temperature
- additiondiluted with EtOAc
- washThe organic layer was washed with water, brine
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by MPLC on silica gel (50% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-8126798c1f1e433dbc65ccfdf559d21b
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328099B2
Reaction notes
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