Pyrrolidine → HCID 53374177, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[5-chloro-7-(tetrahydro-2H-pyran-4-yloxy)pyrazolo[1,5-a]pyrimidin-2-yl]-3-methylquinoxaline (90 mg, 0.227 mmol), pyrrolidine (49 mg, 0.682 mmol), sodium tert-butoxide (33 mg, 0.341 mmol), palladium(II) acetate (52 mg, 0.227 mmol), and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (179 mg, 0.454 mmol) in 1,4-dioxane (4.0 mL) was heated at 100° C. for 40 min. After being cooled to ambient temperature, the reaction mixture was poured into water, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:9) to give 2-methyl-3-[5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-yloxy)pyrazolo[1,5-a]pyrimidin-2-yl]quinoxaline. MS (APCI): m/z 431 (M+H).

Provenance & Evidence