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

Participants

Reaction Conditions

Reaction Steps

428 mg of 3-Bromo-thieno[3,2-b]pyridine (2.0 mmol) is dissolved in 2.0 ml of dry THF and cooled to −78° C. and 0.88 ml of n-BuLi 2.5M in hexane (2.2 mmol) is added slowly and the mixture is stirred at −78° C. for 15 min. 4.4 ml of ZnCl2 0.5M in THF (2.2 mmol) is added and stirred at room temperature for 20 min. 617 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.8 mmol) and 66 mg of PdCl2(dppf) (0.08 mmol) are added. The reaction vial is capped with a Teflon cap and heated at 80° C. overnight. Water and CH2Cl2 are added, and the separated CH2Cl2 layer is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=5:1) to produce the title compound 171 mg (22%), mass spectrum (m/e): 430; 1H-NMR (CDCl3): 8.84 (dd, 1H, J=4.5 Hz, 1.4 Hz), 8.20 (dd, 1H, J=8.4 Hz, 1.4 Hz), 7.37 (dd, 1H, J=8.4 Hz, 4.5 Hz), 6.75 (s, 1H), 3.34 (m, 1H), 2.56 (s, 3H), 2.51 (s, 3H), 1.85 (m, 4H), 0.89 (t, 6H, J=7.4 Hz) ppm.

Provenance & Evidence