Acetic Acid → HCID 178452616, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-Boc-2-aminoindane-2-carboxylic acid (3.30 g, 11.9 mmol) in N,N-dimethylformamide (15.0 mL) and 4-methylmorpholine (2.20 mL, 20.0 mmol) cooled to −20° C. was added a solution of isopropyl chloroformate in toluene (1.0 M, 20.0 mL, 20.0 mmol) dropwise over one hour. The mixture was stirred for an additional 60 minutes at −20° C. and then 4-bromo-1,2-benzenediamine (3.30 g, 17.6 mmol) was added. The reaction mixture was allowed to warm to room temperature for 18 hours. The solvent was evaporated, redissolved in ethyl acetate, washed with water, saturated aqueous solution of sodium hydrogen carbonate, and brine. The organic layer was dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. The resulting residue was dissolved in acetic acid (20.0 mL, 352 mmol) and heated at 60° C. for 2 hours. After cooling, the solvent was removed in vacuo and then purified by silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient to afford the title compound (3.05 g, 60%) as a brown solid.

Provenance & Evidence