2-(4-bromophenyl)-N,N-dimethylacetamide → HCID 118717961, compound

Participants

Reaction Conditions

Reaction Steps

8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (94 mg, 0.40 mmol), 2-(4-bromophenyl)-N,N-dimethylacetamide (103 mg, 0.40 mmol), Cesium carbonate (198 mg, 0.61 mmol), Palladium(II) acetate (9.09 mg, 0.04 mmol) and 2-(Dicyclohexylphosphino)biphenyl (14.18 mg, 0.04 mmol) were added to a 0.5-2 mL microwave vial. The vial was capped and flushed with nitrogen. dioxane (3 mL) was added and the vial was flushed with additional nitrogen before it was heated by microwave irradiation at 120°C for 1.5h. The reaction mixture was cooled to r.t. and water and EtOAc were added and the layers were separated. The aqueous phase was extracted with EtOAc (3x). The combined organic phases were washed with brine, dried (phase separator) and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a gradient of 0-3% MeOH in EtOAc over 12 min. The desired fractions were combined to result in 2-(4-(8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)phenyl)-N,N-dimethylacetamide (51.0 mg, 32.0 %)

Provenance & Evidence