Potassium tert-butoxide → HCID 22347175, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2F)=[N:10][NH2:11])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>CN1C(=O)CCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:11][N:10]=2)=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of N1-(4-bromophenyl)-2-fluoro-1-benzenecarbohydrazonamide (1.2 g, 0.00391 mol) in N-methyl pyrrolidinone (25 mL), potassium tert-butoxide (0.50 g, 0.0041 mol) was added and the resulting solution was heated at 100° C. under an atmosphere of nitrogen for 3 hours. The reaction mixture was cooled to ambient temperature, the solvent was removed under reduced pressure and the residue partitioned between saturated solution of sodium bicarbonate in water (50 mL) and ethyl acetate (50 mL). The organic phase was washed with brine, dried with magnesium sulfate and concentrated. The residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (1:5) as mobile phase to yield N-(4-bromophenyl)-N-(1H-3-indazolyl)amine (0.29 g, 0.0010 mol) as a white solid.
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- customthe solvent was removed under reduced pressure
- customthe residue partitioned between saturated solution of sodium bicarbonate in water (50 mL) and ethyl acetate (50 mL)
- washThe organic phase was washed with brine
- dry with materialdried with magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by flash chromatography on silica
Sources & evidence
- ORD record
- ord-73fa7860fb6f45bb8e2abd9cdc1f4aed
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921763B2
Reaction notes
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