Ethylenediamine → HCID 59548554, compound

Participants

Reaction Steps

A mixture of 4-Bromo-2-fluoro-benzoic acid (500 mg, 2.28 mmol) and 5 mL Ethane-1,2-diamine was reacted in a sealed tube under argon with microwave irradiation at 150 C for 30 min. The reaction was cooled, diluted with methylene chloride (200 mL), and DMF (10 mL) to give a homogeneous solution. 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU), (1 g, 2.63 mmol, 1.1 eq.) was added, and the reaction stirred at room temperature for 2 hours. The reaction was then heated to 95 C for 15 hours, cooled, and 3 mL 5 N NaOH was added. The mixture was stirred at room temperature for 1 hour, the reaction was concentrated in vacuo, extracted with ethyl acetate 3×, the organic layers were dried and concentrated. The residue was purified by flash chromatography to give 150 mg of 8-Bromo-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one, 27%.

Provenance & Evidence