1,2-Dibromoethane → 3-(4-(2-bromoethoxy)-3-chlorophenyl)-7-morpholino-9H-carbazole-1-carboxamide

Participants

Reaction Steps

A 100 ml round bottom flask was loaded with 3-(3-chloro-4-hydroxyphenyl)-7-morpholino-9H-carbazole-1-carboxamide (114.9 mg, 0.245 mmol, Example 406), K2CO3 (386 mg, 2.79 mmol), DMF (10 ml) and 1,2-dibromoethane (0.24 ml, 2.79 mmol) and the mixture stirred at room temperature for 4 hours. The reaction mixture was partitioned between 500 ml water+citric acid (0.5 M solution in water) (20 ml, 10.00 mmol) and ethyl acetate. The organic layer was washed with dilute (1+5) aq. NaHCO3 solution, then brine, dried over MgSO4, filtered and evaporated to dryness to give 118.6 mg 3-(4-(2-bromoethoxy)-3-chlorophenyl)-7-morpholino-9H-carbazole-1-carboxamide. MS (ESI) m/e+=528/530/532, m/e−=526/528/530 consistent with isotope pattern for 1 Br and 1 Cl. 1H NMR (DMSO-d6) δ ppm 11.14 (s, 1H), 8.50 (d, 1H, J=1.5), 8.34 (b, 1H), 8.15 (d, 1H, J=1.6), 8.07 (d, 1H, J=8.5), 8.01 (d, 1H, J=2.2), 7.83 (dd, 1H, J=8.6, 2.4), 7.52 (b, 1H), 7.31 (d, 1H, J=8.8), 7.24 (d, 1H, J=2.0), 6.95 (dd, 1H, J=8.8, 2.2), 4.50 (t, 2H, J=5.5),), 3.89 (t, 2H, J=5.5), 3.83-3.79 (m, 4H), 3.22-3.17 (m, 4H).

Provenance & Evidence