Trimethylphosphine → 4H-Isoxazolo[3,4-d][2]benzazepine, 6-(4-chlorophenyl)-1,4-dimethyl-

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Reaction Steps

To a round bottomed flask was added (2-(3-(1-azidoethyl)-5-methylisoxazol-4-yl)phenyl)(4-chlorophenyl)methanone (0.073 g, 0.199 mmol), toluene, and trimethylphosphine (0.239 mL, 1M in toluene, 0.239 mmol). The reaction was stirred at room temperature overnight before concentrating. The crude residue was purified via Biotage (EtOAc/hex) to afford impure 6-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[c]isoxazolo[4,3-e]azepine. This material was purified via preparatory HPLC and the fractions neutralized before being extracted with EtOAc. The organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 6-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[c]isoxazolo[4,3-e]azepine (0.0011 g, 0.003 mmol). 1H NMR (400 MHz, Acetone-d6) δ 7.74-7.70 (m, 1H), 7.69-7.63 (m, 1H), 7.49-7.41 (m, 3H), 7.41-7.33 (m, 3H), 4.24-4.16 (m, 1H), 2.66 (s, 3H), 1.86 (d, J=6.35 Hz, 3H); LC/MS m/z 323 [M+H]+.

Provenance & Evidence