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

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Reaction Steps

380 mg of 3-Bromo-2-methyl-thieno[3,2-b]pyridine (1.66 mmol) is placed into the vial with 3.56 ml of Reiki Zn, suspension in THF (2.50 mmol) and capped and heated at 100C for 2 h. The excess Zinc is allowed to settle down and the solution is transferred to the vial containing 250 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.72 mmol) and 48 mg of PdCl2(pddf) (0.06 mmol) in 2 ml of dry THF. The vial is capped by Teflon cap and heated at 80C for overnight. The reaction mixture is quenched by sat.NH4Claq. and extracted by CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane: AcOEt: 2 M NH3 in MeOH=20:4:1) to give 24.2 mg of the title compound. Yield 9.2%. mass spectrum (m/e): 365 (M+1); 1H-NMR (CDCl3): 8.66 (dd, 1H, J=4.7 Hz, 1.4 Hz), 8.16 (dd, 1H, J=8.1 Hz, 1.4 Hz), 7.25 (dd, 1H, J=8.1 Hz, 4.7 Hz), 6.68 (s, 1H), 3.43 (m, 1H), 2.50 (s, 3H), 2.47 (s, 3H), 2.46 (s, 3H), 1.88 (m, 4H), 0.93 (m, 6H) ppm.

Provenance & Evidence