2-(2-amino-4-bromoanilino)ethanol

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

Procedure: 2-(2-Amino-4-bromophenylamino)ethanol (700 mg, 3.03 mmol), N-Boc-glycine (639 mg, 3.65 mmol), HATU (1.39 g, 3.66 mmol) and i-Pr2NEt (785 mg, 1.0 mL, 6.09 mmol) were stirred in methylene chloride (20 mL) for 20 min. The mixture was purified by column chromatography eluting with methylene chloride and a 9:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 85% methylene chloride, to provide the title compound (1.26 g, quant) as a yellow oil: ESI MS m/z 388 [M+H]+. The mixture was purified by column chromatography eluting with methylene chloride

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

Procedure: 2-(2-Amino-4-bromophenylamino)ethanol (700 mg, 3.03 mmol), N-Boc-glycine (639 mg, 3.65 mmol), HATU (1.39 g, 3.66 mmol) and i-Pr2NEt (785 mg, 1.0 mL, 6.09 mmol) were stirred in methylene chloride (20 mL) for 20 min. The mixture was purified by column chromatography eluting with methylene chloride and a 9:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 85% methylene chloride, to provide the title compound (1.26 g, quant) as a yellow oil: ESI MS m/z 388 [M+H]+. The mixture was purified by column chromatography eluting with methylene chloride

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(4-Bromo-2-nitrophenylamino)ethanol (3.20 g, 12.3 mmol) was stirred in EtOH (100 mL) and water (50 mL), and iron powder (3.45 g, 61.6 mmol) and ammonium chloride (731 mg, 13.5 mmol) were added. The mixture was heated at 85° C. for 2 h, then filtered through a pad of celite and rinsed with EtOH (500 mL). The filtrate was concentrated and purified by column chromatography eluting with methylene chloride and a 9:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 85% methylene chloride, to provide the title compound (2.58 g, 91%) as a yellow oil: ESI MS m/z 231 [M+H]+. filtered through a pad of celite rinsed with EtOH (500 mL) The filtrate was concentrated purified by column chromatography eluting with methylene chloride

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

Procedure: 2-(2-Amino-4-bromophenylamino)ethanol (700 mg, 3.03 mmol), N-Boc-glycine (639 mg, 3.65 mmol), HATU (1.39 g, 3.66 mmol) and i-Pr2NEt (785 mg, 1.0 mL, 6.09 mmol) were stirred in methylene chloride (20 mL) for 20 min. The mixture was purified by column chromatography eluting with methylene chloride and a 9:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 85% methylene chloride, to provide the title compound (1.26 g, quant) as a yellow oil: ESI MS m/z 388 [M+H]+. The mixture was purified by column chromatography eluting with methylene chloride

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(4-Bromo-2-nitrophenylamino)ethanol (3.20 g, 12.3 mmol) was stirred in EtOH (100 mL) and water (50 mL), and iron powder (3.45 g, 61.6 mmol) and ammonium chloride (731 mg, 13.5 mmol) were added. The mixture was heated at 85° C. for 2 h, then filtered through a pad of celite and rinsed with EtOH (500 mL). The filtrate was concentrated and purified by column chromatography eluting with methylene chloride and a 9:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 85% methylene chloride, to provide the title compound (2.58 g, 91%) as a yellow oil: ESI MS m/z 231 [M+H]+. filtered through a pad of celite rinsed with EtOH (500 mL) The filtrate was concentrated purified by column chromatography eluting with methylene chloride