2-N-(3,5-difluorophenyl)-4-fluorobenzene-1,2-diamine

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

Procedure: A solution of (3,5-difluorophenyl)-(5-fluoro-2-nitrophenyl)amine (2.0 g, 7.5 mmol) in EtOAc (65 mL) was added to a slurry of palladium on carbon (10% by wt, 200 mg) in EtOAc (10 mL) under nitrogen. The reaction mixture was stirred at RT under an atmosphere of hydrogen for 4 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane) to afford the title compound as a white solid that turned red upon standing (1.07 g, 60%). LCMS (Method C): RT 3.40 min [M+H]+ 239. 1H NMR (CDCl3, 400 MHz): δ 6.90-6.87 (1H, m), 6.81-6.73 (2H, m), 6.31-6.23 (3H, m), 5.42 (1H, bs), 3.58 (2H, bs). The mixture was filtered through Celite® the filtrate concentrated in vacuo The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane)

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

Procedure: A solution of (3,5-difluorophenyl)-(5-fluoro-2-nitrophenyl)amine (2.0 g, 7.5 mmol) in EtOAc (65 mL) was added to a slurry of palladium on carbon (10% by wt, 200 mg) in EtOAc (10 mL) under nitrogen. The reaction mixture was stirred at RT under an atmosphere of hydrogen for 4 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane) to afford the title compound as a white solid that turned red upon standing (1.07 g, 60%). LCMS (Method C): RT 3.40 min [M+H]+ 239. 1H NMR (CDCl3, 400 MHz): δ 6.90-6.87 (1H, m), 6.81-6.73 (2H, m), 6.31-6.23 (3H, m), 5.42 (1H, bs), 3.58 (2H, bs). The mixture was filtered through Celite® the filtrate concentrated in vacuo The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane)

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

Procedure: A solution of (3,5-difluorophenyl)-(5-fluoro-2-nitrophenyl)amine (2.0 g, 7.5 mmol) in EtOAc (65 mL) was added to a slurry of palladium on carbon (10% by wt, 200 mg) in EtOAc (10 mL) under nitrogen. The reaction mixture was stirred at RT under an atmosphere of hydrogen for 4 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane) to afford the title compound as a white solid that turned red upon standing (1.07 g, 60%). LCMS (Method C): RT 3.40 min [M+H]+ 239. 1H NMR (CDCl3, 400 MHz): δ 6.90-6.87 (1H, m), 6.81-6.73 (2H, m), 6.31-6.23 (3H, m), 5.42 (1H, bs), 3.58 (2H, bs). The mixture was filtered through Celite® the filtrate concentrated in vacuo The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane)

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

Procedure: A solution of (3,5-difluorophenyl)-(5-fluoro-2-nitrophenyl)amine (2.0 g, 7.5 mmol) in EtOAc (65 mL) was added to a slurry of palladium on carbon (10% by wt, 200 mg) in EtOAc (10 mL) under nitrogen. The reaction mixture was stirred at RT under an atmosphere of hydrogen for 4 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane) to afford the title compound as a white solid that turned red upon standing (1.07 g, 60%). LCMS (Method C): RT 3.40 min [M+H]+ 239. 1H NMR (CDCl3, 400 MHz): δ 6.90-6.87 (1H, m), 6.81-6.73 (2H, m), 6.31-6.23 (3H, m), 5.42 (1H, bs), 3.58 (2H, bs). The mixture was filtered through Celite® the filtrate concentrated in vacuo The resulting residue was purified by column chromatography (Si—PPC, gradient 0-30% EtOAc/cyclohexane)