Potassium Carbonate → 2,6-Dichloro-4-(1-methyl-1H-pyrazol-4-yl)pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH3:10][N:11]1[CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:14]2[CH:13]=[N:12][N:11]([CH3:10])[CH:15]=2)[CH:5]=[C:4]([Cl:9])[N:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
500 mg of 2,6-dichloro-4-iodopyridine, 379 mg of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 753 mg of potassium carbonate and 74 mg of 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride-dichloromethane complex were added in turn to a degassed mixed solvent of 7.5 ml of 1,4-dioxane and 2.5 ml of water, and the mixture was stirred at 90° C. for 2 hours under argon atmosphere. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 257 mg of the objective compound.
Workup
- washThe solution was washed in turn with water and brine
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ca261d59d1d6423b9321fa6ae83291f8
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586591B2
Reaction notes
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