Potassium tert-butoxide → HCID 22346863, compound

HRID 897879Notes

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]1

Participants

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.

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-d66cfd7f72c94b29ab158c95605bb755
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921763B2

Reaction notes

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