4-bromo-2-N-(oxan-4-yl)benzene-1,2-diamine

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(5-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-amine (2.5 g, 8.333 mmol) in EtOH/H2O (1:1) (50 mL) was added iron powder (2.8 g, 50 mmol) and NH4Cl (2.65 g, 50 mmol). The reaction mixture was heated at 60° C. for 12 h. After filtering the reaction mixture, the resulting filtrate was extracted with DCM with the separated organic layer dried over sodium sulfate, filtered and concentrated to obtain crude product which was used in next step without further purification. After filtering the reaction mixture the resulting filtrate was extracted with DCM with the separated organic layer dried over sodium sulfate filtered concentrated to obtain crude product which was used in next step without further purification

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of compound 5-bromo-N1-(tetrahydro-2H-pyran-4-yl)benzene-1,2-diamine (500 mg, 1.852 mmol) in HC(OMe)3 (2 mL) was added TsOH (15 mg, 0.0789 mmol). The reaction mixture was stirred at 100° C. for 12 h. The reaction mixture was extracted with DCM washed with water and the organic layer dried over sodium sulfate which was removed by filtration. After concentration of the filtrate, the crude product was purified by column (201 mg, 38.53%). LCMS (m/z): 281.0, 283.0 (M+1). The reaction mixture was extracted with DCM washed with water the organic layer dried over sodium sulfate which was removed by filtration After concentration of the filtrate, the crude product was purified by column (201 mg, 38.53%)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(5-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-amine (2.5 g, 8.333 mmol) in EtOH/H2O (1:1) (50 mL) was added iron powder (2.8 g, 50 mmol) and NH4Cl (2.65 g, 50 mmol). The reaction mixture was heated at 60° C. for 12 h. After filtering the reaction mixture, the resulting filtrate was extracted with DCM with the separated organic layer dried over sodium sulfate, filtered and concentrated to obtain crude product which was used in next step without further purification. After filtering the reaction mixture the resulting filtrate was extracted with DCM with the separated organic layer dried over sodium sulfate filtered concentrated to obtain crude product which was used in next step without further purification

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(5-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-amine (2.5 g, 8.333 mmol) in EtOH/H2O (1:1) (50 mL) was added iron powder (2.8 g, 50 mmol) and NH4Cl (2.65 g, 50 mmol). The reaction mixture was heated at 60° C. for 12 h. After filtering the reaction mixture, the resulting filtrate was extracted with DCM with the separated organic layer dried over sodium sulfate, filtered and concentrated to obtain crude product which was used in next step without further purification. After filtering the reaction mixture the resulting filtrate was extracted with DCM with the separated organic layer dried over sodium sulfate filtered concentrated to obtain crude product which was used in next step without further purification