Pyrazole → 2-(1H-pyrazol-1-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole
Reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[C:4]=2[CH:3]=1.[NH:21]1[CH:25]=[CH:24][CH:23]=[N:22]1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>[Cu]I>[N:21]1([C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]([CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][O:16]4)[C:4]=3[CH:3]=2)[CH:25]=[CH:24][CH:23]=[N:22]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Under a nitrogen atmosphere, 10 mmol of 2-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole, 15 mmol of pyrazole, 1 mmol of copper(I)iodide, 25 mmol of potassium carbonate, and 2 mmol of L-proline were combined in 25 mL of stirring degassed dimethyl sulfoxide. The mixture was heated to 90° C. for 3 days before being cooled and separated between dichloromethane and water. The water layer was washed twice with dichloromethane and the organics were combined and washed once with brine. The organic fraction was dried with magnesium sulfate and concentrated under reduced pressure and subjected to column chromatography of silica with dichloromethane as the eluent. After concentrating under reduced pressure, 2-(1H-pyrazol-1-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole was isolated in a 40% yield.
Workup
- customdegassed dimethyl sulfoxide
- temperaturebefore being cooled
- customseparated between dichloromethane and water
- washThe water layer was washed twice with dichloromethane
- washwashed once with brine
- dry with materialThe organic fraction was dried with magnesium sulfate
- concentrationconcentrated under reduced pressure
- concentrationAfter concentrating under reduced pressure
Sources & evidence
- ORD record
- ord-a8647f4ff43448d8a79412c80779f585
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238668B2
Reaction notes
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