Triethylamine → HCID 24963706, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of phenyl 6-bromopyridin-3-ylcarbamate (1.03 g, 3.5 mmol) in DMSO (5 mL) was added 2-(3-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (1.3 g, 3.51 mmol) followed by triethylamine (0.98 mL, 7.01 mmol). The reaction was stirred at 60° C. overnight and then allowed to cool to RT. The reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4 and concentrated. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl2) afforded the title compound as an oil, which foamed up on the pump (1.76 g, 94% yield). MS (APCI 10V) AP+2 535.08; 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (t, 2H) 2.59 (t, 2H) 3.50 (t, 2H) 3.59 (t, 2H) 6.40 (s, 1H) 6.47 (br. s., 1H) 6.97-7.03 (m, 3H) 7.08 (d, 1H) 7.36-7.41 (m, 2H) 7.87-7.92 (m, 2H) 8.20 (d, 1H) 8.43 (d, 1H).

Provenance & Evidence