(2-Amino-5-bromophenyl)(2-fluorophenyl)methanone → 9H-fluoren-9-ylmethyl [2-({4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}amino)-2-oxoethyl]carbamate

Participants

Reaction Steps

A round-bottomed flask was charged with (2-amino-5-bromophenyl)(2-fluorophenyl)methanone (1.45 g), 9H-fluoren-9-ylmethyl (2-chloro-2-oxoethyl)carbamate (1.6 g) and chloroform (150 mL). The mixture was heated to reflux for 2 h then concentrated to dryness. The residue was taken up in a mixture of a saturated solution of sodium bicarbonate and ethyl acetate. The resulting solids were collected on a filter and washed first with water then with diethyl ether. Thorough air-drying provided 9H-fluoren-9-ylmethyl [2-({4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}amino)-2-oxoethyl]carbamate (2 g) as a light yellow powder. H1 NMR (d6-dmso): 10.8 (br s, 1H), 7.95 (d, 1H), 7.75-7.90 (m, 4H), 7.45-7.70 (m, 5H), 7.20-7.42 (m, 6H), 4.30 (d, 2H), 4.20 (t, 1H), 3.65 (d, 2H).

Provenance & Evidence