反应详情

温度

130 °C

A mixture of N-[6-bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide (Int. 18, 0.5 g, 1.21 mmol) was combined with ethyl-1-propenyl ether (125 mg, 1.45 mmol), triethylamine (202 μL, 1.45 mmol), palladium (II) acetate (3 mg, 0.012 mmol), tri-O-tolylphosphine (15 mg, 0.048 mmol) in DMF (7 mL) was degassed and then heated at 130° C. for 5 hrs. Further amounts of palladium (II) acetate (3 mg) and ethyl-1-propenyl ether (125 mg) were added and heating was continued for 5 days. 1 M HCl (5 mL) was added and the mixture was stirred vigorously for 40 mins. The mixture was partitioned between EtOAc (100 mL) and water (100 mL) and the organic layer was washed with saturated brine, then dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by chromatography, eluting with a gradient of 0-10% MeOH in DCM followed by trituration with DCM and ether. The resultant precipitate was collected by filtration and dried to afford the title compound as a white solid (11%)

1. customwas degassed
2. additionFurther amounts of palladium (II) acetate (3 mg) and ethyl-1-propenyl ether (125 mg) were added
3. temperatureheating
4. addition1 M HCl (5 mL) was added
5. customThe mixture was partitioned between EtOAc (100 mL) and water (100 mL)
6. washthe organic layer was washed with saturated brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customThe resultant residue was purified by chromatography
10. washeluting with a gradient of 0-10% MeOH in DCM
11. filtrationThe resultant precipitate was collected by filtration
12. customdried