反应详情

温度

100 °C

4-bromo-N-methyl-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (1.0 equiv, 0.82 mmol), 7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (1.5 equiv, 1.23 mmol), Cs2CO3 (3.0 equiv, 2.46 mmol), Pd2(dba)3 (0.1 equiv, 0.082 mmol), and Xantphos (0.2 equiv, 0.1634 mmol) were dissolved in 15 mL dioxane and purged of air, then placed under an argon blanket and refluxed for 18 h at 100° C. The reaction was cooled to room temperature and filtered and condensed under reduced pressure. The residue that was recovered was dissolved in EtOAc and extracted with saturated bicarbonate and brine; the organics were then dried (Na2SO4) and concentrated to afford brown oil. Using EtOAc/hexanes (1:5 v/v) the residue was precipitated out to afford 4-[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-methyl-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide, as a tan solid, (297.2 mg, 76% yield). 1H NMR (DMSO-d6): δ 1.95 (dm, 4H), 2.72 (s, 3H), 2.73 (s, 3H), 3.04 (q, J=7.5 Hz, 2H), 3.35 (dt, J=5.3 Hz, J=5.4 Hz, 4H), 3.58 (q, J=5.2 Hz, 2H), 7.52 (t, J=7.6 Hz, 1H), 7.67 (d, J=3.2 Hz, 2H), 7.79 (s, 1H), 7.87 (d, J=3.2 Hz, 2H), 8.18 (s, 1H), 8.31 (s, J=9.0 Hz, 2H), 10.51 (bs, 1H), 11.55 (s, 1H). MS (ES+) m/z=574, LC retention time 2.80 minutes.

1. custompurged of air
2. temperatureThe reaction was cooled to room temperature
3. filtrationfiltered
4. customcondensed under reduced pressure
5. customThe residue that was recovered
6. dissolutionwas dissolved in EtOAc
7. extractionextracted with saturated bicarbonate and brine
8. dry with materialthe organics were then dried (Na2SO4)
9. concentrationconcentrated
10. customto afford brown oil
11. customUsing EtOAc/hexanes (1:5 v/v) the residue was precipitated out