Diisopropylethylamine → 4-(3-(5-bromopyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

5-Bromo-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate (1 mmol, from Step 5), in acetonitrile (3 mL) was treated with ethyl pyridazin-3-ylcarbamate (184 mg, 1.10 mmol) and diisopropylethylamine (0.52 mL, 3.00 mmol) and was heated to 180° C. in a microwave for 40 min. The reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel (0-6% ethanol (containing 11% aq NH4OH):dichloromethane) to afford a light yellow foam (168 mg, 36% yield). MS (APCI) M+1=466.0; 1H NMR (400 MHz, CDCl3) δ ppm 2.48 (t, J=5.46 Hz, 2H) 2.58-2.65 (m, 2H) 3.60 (t, J=5.75 Hz, 2H) 3.65-3.74 (m, 2H) 6.42 (s, 1H) 6.86 (dd, J=8.67, 0.49 Hz, 1H) 6.96-7.03 (m, 2H) 7.07 (d, J=7.60 Hz, 1H) 7.38 (t, J=7.80 Hz, 1H) 7.44 (dd, J=9.16, 4.48 Hz, 1H) 7.79 (dd, J=8.77, 2.53 Hz, 1H) 8.24 (dd, J=2.53, 0.39 Hz, 1H) 8.26-8.37 (m, 1H) 8.79 (br. s, 1H).

Herkunft & Nachweise