Boron tribromide → HCID 11634592, compound

Participants

Reaction Steps

[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[3-(2-pyrrolidin-1-yl-ethylsulfanyl)-phenyl]-amine (1.0 equiv., 0.62 mmol) was dissolved in anhydrous DCM, purged of air using house vacuum, and placed under an argon blanket. Neat BBr3 (4.0 equiv., 2.5 mmol) was then added via syringe and allowed to stir at room temperature for 2 h. The reaction was quenched using saturated NaHCO3; the precipitate was filtered and washed with water and Et2O to afford a dark orange/brown solid. The compound was purified by flash chromatography using 90:10 DCM/MeOH to recover a burnt orange solid (64.6 mg, 22% yield). Rf=0.32 1H NMR (DMSO-d6): δ 1.68 (bs, 4H), 2.68 (s, 3H), 2.73 (bs, 2H), 3.14 (t, J=6.87 Hz, 2H), 6.87 (d, J=8.10 Hz, 1H), 6.93 (s, 1H), 7.03 (d, J=7.42 Hz, 1H), 7.34 (t, J=7.58 Hz, 1H), 7.40 (d, J=8.65 Hz, 1H), 7.77 (d, J=7.95 Hz, 1H), 8.16 (s, 2H), 9.93 (s, 1H), 11.01 (s, 1H). MS (ES+): m/z=493

Provenance & Evidence