2,4-Dichloropyridine → HCID 101584496, compound

Participants

Reaction Conditions

Reaction Steps

Repeat of EN04881-41 to get pure sample of product in potentially higher isolated yield. cesium carbonate (652 mg, 2.00 mmol), Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 4-(trifluoromethyl)oxazol-2-amine (152 mg, 1.00 mmol) and 2,4-dichloropyridine (148 mg, 1.00 mmol) were added to an oven dried microwave vial, the vial was capped and placed under an inert atmosphere, dioxane (4 mL) was added and the resulting mixture was heated at 140 °C for 1 h by microwave irradiation under a nitrogen atmosphere. Dichloromethane (10 mL) was added to the reaction mixture and the crude reaction mixture was adsorbed onto silica gel. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in heptane. Pure fractions were evaporated to dryness to afford N-(4-chloropyridin-2-yl)-4-(trifluoromethyl)oxazol-2-amine (46.0 mg, 17.45 %) as a pale yellow solid. Regioisomeric assignment confirmed by NOESY experiment (see sample P1 analytical data for details).

Provenance & Evidence