1-Ethylpiperazine → 8-[[5-(4-Ethyl-1-piperazinyl)-2-(trifluoromethoxy)phenyl]amino]-4,5-dihydro-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Participants

Reaction Steps

Tris(dibenzilideneacetone)dipalladium, Pd2(dba)3, (9.1 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (7.8 mg, 0.02 mmol), 8-[2-trifluoromethoxy-5-bromo-phenylamino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (200 mg, 0.41 mmol) in THF (4.5 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. LiN(TMS)2 solution (1M in THF, 2.7 mL) and N-ethylpiperazine (0.125 mL, 0.98 mmol) were added and the reaction mixture refluxed for 3 h. The reaction mixture was then allowed to cool to room temperature and concentrated. The crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 46 mg (52% yield) of the title compound.

Provenance & Evidence