Sodium Carbonate → 7-Amino-3-m-tolyl-9H-carbazole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

7-Amino-3-bromo-9H-carbazole-1-carboxamide 470B (350 mg, 1.151 mmol), m-tolylboronic acid (313 mg, 2.302 mmol), PdCl2(dppf)-CH2Cl2 adduct (94 mg, 0.115 mmol), and Na2CO3 (2M) (2.88 mL, 5.75 mmol) were mixed with DME (15 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 316.04 (M+H)+. 1H NMR (DMSO-d6) δ ppm 10.89 (s, 1H), 8.30 (s, 1H), 8.23 (s, 1H), 8.03 (s, 1H), 7.82 (d, 1H, J=8.2), 7.67 (s, 1H), 7.63 (d, 1H, J=7.6), 7.41(s, 1H), 7.36 (t, 1H, J=7.6), 7.14 (d, 1H, J=7.6), 6.81 (s, 1H), 6.5 (d, 1H, J=8.3), 5.24 (bs, 2H), 2.42 (s, 3H).

Provenance & Evidence