Boron tribromide → 3-[[7-(2-Chloro-5-hydroxyphenyl)-5-methyl-1,2,4-benzotriazin-3-yl]amino]-N-[2-(dimethylamino)ethyl]benzenesulfonamide

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Reaction Steps

3-[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-dimethylamino-ethyl)-benzenesulfonamide (0.32 mmol, 1.0 equiv) was dissolved in 10 mL of anhydrous DCM and placed under an argon atmosphere. 4 mL of BBr3 (0.1 M) added via syringe and the reaction stirred at room temperature for 2 h. BBr3 was quenched with saturated NaHCO3 until pH=7. The mixture was filtered and washed with water and Et2O to give 3-[7-(2-chloro-5-hydroxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-dimethylamino-ethyl)-benzenesulfonamide, as an orange solid (132.2 mg, 81% yield). 1H NMR (DMSO-d6): δ 2.71 (s, 2H), 3.01 (bs, 2H), 6.87 (dd, J=8.8 Hz, J=2.9 Hz, 1H), 6.94 (d, J=3.0 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.51 (d, J=7.9 Hz, 1H), 7.64 (t, J=8.1 Hz, 2H), 7.90 (s, 1H), 8.06 (d, J=6.7 Hz, 1H), 8.20 (s, 1H), 8.89 (s, 1H), 9.93 (s, 1H), 11.34 (s, 1H). MS (ES+) m/z=513. LC retention time 2.24 min.

Provenance & Evidence