(NE)-N-(5-bromo-2,3-dihydroinden-1-ylidene)hydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromoindan-1-one (5.0 g) was dissolved in methanol. Hydroxylammonium chloride (2.5 g) and sodium acetate (2.9 g) were added to the solution at room temperature, and then stirred overnight. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The desiccant was filtered and separated, and then the solvent was evaporated off under reduced pressure to obtain 5-bromo-N-hydroxyindan-1-imine (5.1 g). extracted twice with ethyl acetate washed with water dried over anhydrous magnesium sulfate The desiccant was filtered separated the solvent was evaporated off under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromoindan-1-one (5.0 g) was dissolved in methanol. Hydroxylammonium chloride (2.5 g) and sodium acetate (2.9 g) were added to the solution at room temperature, and then stirred overnight. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The desiccant was filtered and separated, and then the solvent was evaporated off under reduced pressure to obtain 5-bromo-N-hydroxyindan-1-imine (5.1 g). extracted twice with ethyl acetate washed with water dried over anhydrous magnesium sulfate The desiccant was filtered separated the solvent was evaporated off under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 5-bromoindan-1-one oxime and 4-cyanophenyl boronic acid according to the procedure described in example 6. MS (ESI) m/z 249; HRMS: calcd for C16H12N2O+H+, 249.10224; found (ESI, [M+H]+), 249.1021.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 5-bromoindan-1-one oxime and 4-cyanophenyl boronic acid according to the procedure described in example 6. MS (ESI) m/z 249; HRMS: calcd for C16H12N2O+H+, 249.10224; found (ESI, [M+H]+), 249.1021.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 5-bromoindan-1-one oxime (0.25 g, 1.10 mmol) in glyme (11 mL) was added 3-cyanophenyl boronic acid (0.21 g, 1.44 mmol), sodium carbonate (0.35 g, 3.30 mmol) dissolved in deionized (D.I.) water (2 mL), and tetrakis(triphenylphosphine) palladium (0) (0.06 g, 0.05 mmol). The resulting solution was heated to reflux for 2 hours. The solution was cooled to room temperature and partitioned between ammonium chloride solution (sat.) and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a silica gel column (20% ethyl acetate/hexane) and triturated with ether to give 3-[(1E)-1-(hydroxyimino)-2,3-dihydro-1H-inden-5-yl]benzonitrile as a white solid (0.12 g, 43%). MS (ESI) m/z 249; HRMS: calcd for C16H12N2O+H+, 249.10224; found (ESI, [M+H]+), 249.1033. The resulting solution was heated to reflux for 2 hours partitioned between ammonium chloride solution (sat.) and ethyl acetate The organic layer was dried over magnesium sulfate filtered concentrated The residue was purified on a silica gel column (20% ethyl acetate/hexane) triturated with ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromoindan-1-one (5.0 g) was dissolved in methanol. Hydroxylammonium chloride (2.5 g) and sodium acetate (2.9 g) were added to the solution at room temperature, and then stirred overnight. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The desiccant was filtered and separated, and then the solvent was evaporated off under reduced pressure to obtain 5-bromo-N-hydroxyindan-1-imine (5.1 g). extracted twice with ethyl acetate washed with water dried over anhydrous magnesium sulfate The desiccant was filtered separated the solvent was evaporated off under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromoindan-1-one (5.0 g) was dissolved in methanol. Hydroxylammonium chloride (2.5 g) and sodium acetate (2.9 g) were added to the solution at room temperature, and then stirred overnight. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The desiccant was filtered and separated, and then the solvent was evaporated off under reduced pressure to obtain 5-bromo-N-hydroxyindan-1-imine (5.1 g). extracted twice with ethyl acetate washed with water dried over anhydrous magnesium sulfate The desiccant was filtered separated the solvent was evaporated off under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromoindan-1-one (5.0 g) was dissolved in methanol. Hydroxylammonium chloride (2.5 g) and sodium acetate (2.9 g) were added to the solution at room temperature, and then stirred overnight. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The desiccant was filtered and separated, and then the solvent was evaporated off under reduced pressure to obtain 5-bromo-N-hydroxyindan-1-imine (5.1 g). extracted twice with ethyl acetate washed with water dried over anhydrous magnesium sulfate The desiccant was filtered separated the solvent was evaporated off under reduced pressure