Potassium tert-butoxide → HCID 22346863, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[N:17][OH:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2F)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>CN1CCCC1=O>[O:18]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[N:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of N1-(4-bromophenyl)-2-fluoro-1-benzeneamidoxime (1.51 g, 0.00489 mol) in N-methylpyrrolidinone (25 mL), potassium tert-butoxide (0.54 g, 0.00513 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-benzo[d]isoxazol-3-yl-N-(4-bromophenyl)amine (0.95 g, 0.00329 mol) as a white solid.