1,2-Dichloroethane → 4-(2-fluorophenyl)-7-(morpholine-4-carbonyl)-9H-pyrido[3,4-b]indole-1-carboxamide

Participants

Reaction Steps

To a yellow, heterogeneous solution of 4-(2-fluorophenyl)-7-(morpholine-4-carbonyl)-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.0381 g, 0.091 mmol), ammonium chloride (9.72 mg, 0.182 mmol), HOAt (0.025 g, 0.182 mmol) and EDC (0.035 g, 0.182 mmol) in DMF (1.0 mL) was added DIPEA (0.063 mL, 0.364 mmol). The reaction was stirred overnight. EtOAc and water were added, and the layers were separated. The organic layer was washed with brine and 10% aq. LiCl successively, dried over Na2SO4, filtered and concentrated in vacuo to give a residue which was diluted with MeOH (1 mL) and subjected to autoprep reverse phase HPLC purification. The appropriate fractions were combined, basified with NaHCO3 (solid), and concentrated in vacuo. It was extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4, and concentrated in vacuo to give the desired product (0.0124 g, 0.030 mmol, 32.6% yield) as a white solid. LC/MS (M+H)=419.08; 1H NMR (500 MHz, DMSO-d6) δ ppm 12.03 (s, 1H), 8.38 (br. S, 1H), 8.32 (s, 1H), 7.89 (s, 1H), 7.86 (br. S, 1H), 7.63-7.75 (m, 2H), 7.44-7.58 (m, 2H), 7.34 (d, J=8.2 Hz, 1H), 7.13 (d, J=8.2 Hz, 1H), 3.42-3.83 (m, 8H).

Provenance & Evidence