Hexane → 3-(3-Chloro-thieno[2,3-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Participants

Reaction Conditions

Reaction Steps

250 mg of 3-Chloro-thieno[2,3-b]pyridine (1.5 mmol) is dissolved in 2.0 ml of dry THF and cooled to −78° C. 0.59 ml of n-butyl lithium 2.5 M in hexane (1.5 mmol) is added slowly and stirred at room temperature for 3 min and cooled to −78° C. 3.0 ml of 0.5 M ZnCl2 in THF (1.5 mmol) is added and stirred at room temperature for 20 min. 343 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.0 mmol) and 41 mg of PdCl2(dppf) (0.05 mmol) are added and the reaction vial is capped with a Teflon cap and heated at 80° C. overnight. The reaction mixture is concentrated and applied onto a chromatography silica-gel column (Hexane:AcOEt=3:1); mass spectrum (m/e): 385; 1H-NMR (CDCl3): 8.66 (dd, 1H, J=4.5 Hz, 1.5 Hz), 8.10 (dd, 1H, J=8.1 Hz, 1.5 Hz), 7.44 (1H, J=8.1 Hz, 4.5 Hz), 6.74 (s, 1H), 3.33 (m, 1H), 2.55 (s, 3H), 2.53 (s, 3H), 1.85 (m, 4H), 0.89 (t, 6H, J=7.5 Hz) ppm.

Provenance & Evidence