1,2-Dichloroethane → 3-(3-Methoxyphenyl)-7-(4-morpholinylcarbonyl)-9h-carbazole-1-carboxamide

Participants

Reaction Steps

A mixture of 8-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carboxylic acid (36 mg, 0.100 mmol), morpholine (17 mg, 0.2 mmol), EDC (23 mg, 0.12 mmol), HOBt (18 mg, 0.12 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.035 mL, 0.2 mmol) in a mixture of THF (5 mL) and CH2Cl2 (1 mL) was stirred at room temperature overnight. This was diluted with MeOH and the product was isolated by preparative HPLC (100×30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B=90:10 and ending with A:B=30:70 [A=10 mM NH4OAc in 5% aqueous acetonitrile; B=10 mM NH4OAc in 95% aqueous acetonitrile] over 20 min) followed by removal of the solvents. This afforded 29 mg of 3-(3-methoxyphenyl)-7-(morpholine-4-carbonyl)-9H-carbazole 1-carboxamide as a solid. MS (ESI) m/z 430.2 (M+H). 1H NMR (MeOD) δ ppm 8.42 (1H, s), 8.13 (1H, d, J=7.94 Hz), 8.05 (1H, s), 7.57 (1H, s), 7.32-7.41 (2H, m), 7.29 (1H, d, J=7.63 Hz), 7.21-7.26 (1H, m), 6.85-6.93 (1H, m), 3.88 (3H, s), 3.43-3.84 (8H, m).

Provenance & Evidence