1,2-Dimethoxyethane → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

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Reaction Steps

3-Iodo-2,6-dimethyl-8-(1-ethyl-propyl)-imidazo[1,2-b]pyridazine (200 mg, 0.582 mmol), 1,3,5-trimethylpyrazole-4-boronic acid (233 mg, 1.53 mmol), Pd(PPh3)4 (13.4 mg, 0.01 mmol) are combined in a microwave pressure tube. Then 0.58 ml of 2N Na2CO3 and 3.0 ml of dimethoxyethane/H20/ethanol (7:3:2) solution is added. The mixture is microwaved at 155° C. for 20 minutes. Water is added and the mixture is extracted four times with ethyl acetate. The combined organics are dried over MgSO4, filtered, then evaporated to a residue which is chromatographed using hexanes, then 1:1 hexanes:ethyl acetate, then 100% ethyl acetate to give the title compound (6.4%) as a yellow oil. 1H-NMR (DMSO-d6): δ6.86 (s, 1H); 3.73 (s, 3H); 3.06-3.10 (m, 1H); 2.41 (s, 3H); 2.22 (s, 3H); 2.03 (s, 3H); 1.93 (s, 3H); 1.74-1.83 (m, 4H); 0.77 (t, J=7.26 Hz, 6H) ppm. MS/ES+=327 (100%, M+2).

Provenance & Evidence