2,4-Dichloropyridine → 4-chloro-N-(2-methylpyrazol-3-yl)pyridin-2-amine

Temperature

105 °C

TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (251 mg, 0.27 mmol) was [AP-added] to 2,4-dichloropyridine (1000mg, 6.76 mmol), 1-methyl-1H-pyrazol-5-amine (722 mg, 7.43 mmol), cesium carbonate (3302 mg, 10.14 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (461 mg, 0.80 mmol) in 1,4-dioxane (75 mL) warmed to 105ºC over a period of 21 hours under nitrogen. The reaction mixture was evaporated to dryness and redissolved in DCM (50 mL), and sequentially with water (25 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 (710 mg, 50.4 %) as a brown oil.

ORD record

ord-90d260fec9dd4d62a1593e5cdff9b43a

Source dataset

750 AstraZeneca ELN dataset

Original link

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