4-Methylmorpholine → 4-(2-Fluorophenyl)-7-methyl-6-(pyrimidin-5-yloxy)-9H-pyrido[3,4-b]indole-1-carboxamide

Participants

Reaction Steps

A sealed vial containing 4-(2-fluorophenyl)-7-methyl-6-(pyrimidin-5-yloxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.0456 g, 0.110 mmol), ammonium chloride (0.024 g, 0.440 mmol), benzotriazole-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (0.063 g, 0.143 mmol), DIPEA (0.092 mL, 0.528 mmol) and N-methylmorpholine (0.047 mL, 0.429 mmol) in DMF (0.8 mL) was stirred. After 1 hr, the reaction 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 (0.0137 g, 0.033 mmol, 30.1% yield) as a light tan solid, LC/MS (M+H)=414.10; 1H NMR (500 MHz, DMSO-d6) δ ppm 11.87 (br. S, 1 H), 8.98 (s, 1H), 8.47 (s, 2H), 8.33 (br. S, 1H), 8.26 (s, 1H), 7.81 (s, 2H), 7.59 (dd, J1=7.49, J2=1.39 Hz, 1H), 7.48-7.54 (m, 1H), 7.22-7.33 (m, 2H), 6.72 (s, 1H), 2.35 (s, 3 H).

Provenance & Evidence