HCID 23560772, compound → HCID 23560799, compound

Participants

Reaction Conditions

Reaction Steps

Iron powder (135 mg, 2.4 mmol) was added to a suspension of 2-bromo-4-[[(3-nitrobenzyl)amino]carbonyl]benzoic acid methyl ester (Example 85; 125 mg, 3.18 mmol) in water (530 μL) and acetic acid (111 μL) at 25° C. The reaction was heated to reflux for 30 min and then cooled to 25° C. The suspension was diluted with water (20 mL), stirred 15 min, filtered over Celite® and washed well with water (100 mL). The filtrate was washed with ethyl acetate (50 mL) followed by ethyl acetate containing 2% methanol (50 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated. The residue was diluted with 10% methanol in dichloromethane and stirred with Celite®. After 1 h, the suspension was filtered and washed well with 10% methanol in dichloromethane and the combined filtrates were evaporated to dryness to give 2-bromo-4-[[(3-aminobenzyl)amino]carbonyl]benzoic acid methyl ester (100 mg, 87% yield) as an off-white solid.

Provenance & Evidence