Boron tribromide → 4-Chloro-3-[5-methyl-3-[4-(4-methyl-piperazine-1-sulfonyl)-phenylamino]-benzo[1,2,4]triazin-7-yl]-phenol

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Reaction Steps

[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-amine (1.0 equiv., 0.339 mmol) was dissolved in 10 mL anhydrous DCM, purged of air via house vacuum, then blanketed with argon. Neat BBr3 (4.0 equiv., 1.355 mmol) was added via syringe dropwise and allowed to stir at room temperature for 2 h. The reaction was quenched with saturated NaHCO3; the precipitate was filtered and rinsed with Et2O to afford crude orange solid. The compound was purified by prep. HPLC using 10-50-75 gradient, collecting peaks for 9-14 minutes. A yellow solid was recovered (70.5 mg, 40% yield). 1H NMR (DMSO-d6): δ 1.98 (s, 3H), 2.37 (bs, 4H), 2.72 (s, 3H), 2.90 (bs, 4H), 6.88 (dd, J=2.94 Hz, 8.81 Hz, 1H), 6.95 (d, J=2.92 Hz, 1H), 7.41 (d, J=8.79 Hz, 1H), 7.78 (d, J=8.89 Hz, 2H), 7.92 (m, 1H), 8.21 (d, J=1.35 Hz, 1H), 8.28 (d, J=8.88 Hz, 2H), 11.47 (s, 1H). MS (ES+): m/z=526 LC retention time: 2.30 minutes.

Provenance & Evidence