Sodium Carbonate → 7-(4-benzylpiperazin-1-yl)-3-m-tolyl-9H-carbazole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

7-(4-Benzylpiperazin-1-yl)-3-bromo-9H-carbazole-1-carboxamide (100 mg, 0.216 mmol), m-tolylboronic acid (58.7 mg, 0.432 mmol), PdCl2(dppf)-CH2Cl2 adduct (17.62 mg, 0.022 mmol), and Na2CO3 (2M) (0.432 mL, 0.863 mmol) were mixed with DME (4 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 100° C. in an oil bath for 4 hrs. The mixture was purified using preparative HPLC to give titled product. MS (ESI) m/z 475.12 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.07 (s, 1H), 8.44 (s, 1H), 8.28 (s, 1H), 8.12 (s, 1H), 8.02 (d, 1H, J=8.6), 7.69 (s, 1H), 7.65 (d, 1H, J=7.0), 7.47(s, 1H), 7.36 (m, 5H), 7.28 (m, 1H), 7.21 (s, 1H), 7.16 (d, 1H, J=7.9), 6.90 (dd, 1H, J=8.5, 2.1), 3.56 (s, 2H), 3.22 (bm, 4H), 2.57 (bm, 4H), 2.42 (s, 3H).

Provenance & Evidence