6-Chloro-3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine → 3-(6-Fluoro-1-methyl-1H-indazol-5-ylmethyl)-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazine

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Reaction Steps

6-Chloro-3-(6-fluoro-1-methyl-1H-indazol-5-ylmethyl)-imidazo[1,2-b]pyridazine (Stage 281.2, 268 mg, 849 μmol) was introduced in a microwave reactor together with 1-[2-(tetrahydropyran-2-yloxy)-ethyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (Stage 171.4, 410 mg, 1.273 mmol) and DME (5 mL). The mixture was purged with Argon for 5 min. Tetrakis-(triphenylphosphine)-palladium (39.2 mg) and 2 M Na2CO3 (1.528 mL) were added and the mixture was flushed with argon before being sealed. The RM was submitted to microwave irradiation at 150° C. 30 min. The RM was diluted with EtOAc and washed with water, brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with 40 g RediSep® silica gel column, DCM/MeOH=100:0->94:6 in 45 min). The collected fractions containing product were evaporated and the residue was dried under vacuum to afford the title compound as an oil (tR 1.13 min (conditions 2), MH+=476)

Provenance & Evidence