Tricyclohexylphosphine → 6-(6-Methylpyrazin-2-yl)-1-tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridine

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A mixture of tributyl-(1-tetrahydropyran-2-ylpyrazolo[4,3-c]pyridin-6-yl)stannane (7.139 mmol; 3514.5 mg), 2-chloro-6-methyl-pyrazine (10.71 mmol; 1377 mg), tricyclohexylphosphine; (0.5140 mmol; 144.1 mg) and tris(dibenzylideneacetone)dipalladium (0) (0.2142 mmol; 196.1 mg) in N,N-Dimethylacetamide (15 mL) was purged with Argon for 1 min. The reaction mixture was sealed in a pressure vial and heated at 130° C. overnight. The mixture was partitioned between EtOAc and water. The organic layer was concentrated and the residue was purified on silica eluted with 0 to 100% EtOAc in DCM to afford 6-(6-methylpyrazin-2-yl)-1-tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridine as a clear oil (1.3608 g, 60%).

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