Clc1ccnc(Cl)c1.Cn1nccc1N>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>Cn1nccc1Nc1cc(Cl)ccn1TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (124 mg, 0.14 mmol) was added in one portion to 2,4-dichloropyridine (200 mg, 1.35 mmol), 1-methyl-1H-pyrazol-5-amine (158 mg, 1.62 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (156 mg, 0.27 mmol), and cesium carbonate (881 mg, 2.70 mmol) in 1,4-dioxane (20 mL) under nitrogen. The resulting mixture was stirred at 105°C for 2 hours. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL), and washed with water (50 mL). The organic layer was filtered using phase separating paper and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-chloro-N-(1-methyl-1H-pyrazol-5-yl)pyridin-2-amine (66.0 mg, 23.41 %) as a yellow oil which solidified on standing.
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