Potassium Carbonate → 4-(3-methyl-5-nitrophenyl)-1H-pyrazole
Reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12](C(OC(C)(C)C)=O)[CH:13]=2)O1.C(=O)([O-])[O-].[K+].[K+].Br[C:29]1[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=[C:31]([CH3:38])[CH:30]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:38][C:31]1[CH:30]=[C:29]([C:9]2[CH:13]=[N:12][NH:11][CH:10]=2)[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (8.17 g, 27.8 mmol), tetrakis(triphenylphosphine)palladium(0) (2.67 g, 2.31 mmol) and potassium carbonate (12.8 g, 93.0 mmol) were added to a solution of 1-bromo-3-methyl-5-nitrobenzene (5.0 g, 23.1 mmol) in dioxane (7.5 mL). The mixture was degassed with nitrogen for 5 minutes and stirred at 100° C. for 18 h. The mixture was passed through CELITE, washed with methanol and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane) to afford 4-(3-methyl-5-nitrophenyl)-1H-pyrazole. MS ESI calc'd. for C10H10N3O2 [M+H]+ 204. found 204.
Workup
- customThe mixture was degassed with nitrogen for 5 minutes
- washwashed with methanol
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane)
Sources & evidence
- ORD record
- ord-c99db3a547fb4a4483342984073931fb
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242984B2
Reaction notes
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