Triethylamine → N-1H-pyrrolo[2,3-b]pyridin-6-yl-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene) piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of phenyl 1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate (0.150 g, 0.60 mmol, from Step 1) in DMSO (5 mL) was added 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (0.22 g, 0.60 mmol) (from Example 1, Step 5), followed by the addition of triethylamine (0.17 mL, 1.2 mmol). The reaction mixture was stirred at 60° C. overnight. The reaction mixture was cooled down and EtOAc (30 mL) was added. The organic layer was washed with water, saturated NH4Cl, and brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography (0-5% MeOH/CH2Cl2) gave a foam. Diethyl ether was added and a precipitate formed which was collected by filtration to give the title compound (208 mg). MS (M+1): 494.19; 1H NMR (400 MHz, DMSO-d6) δ ppm 11.38-11.40 (m, 1H) 8.54-8.56 (m, 1H) 8.46-8.49 (m, 1H) 8.20 (dd, 1H) 8.15 (d, 1H) 7.92-7.94 (m, 1H) 7.34-7.42 (m, 2H) 7.21 (d, 1H) 7.11-7.15 (m, 1H) 7.02-7.06 (m, 2H) 6.37-6.40 (m, 1H) 6.31-6.34 (m, 1H) 3.55 (t, 2H) 3.47 (t, 2H) 3.28-3.30 (m, 1H) 2.50-2.51 (m, 1H) 2.34 (t, 2H).

Provenance & Evidence