Aniline → Phenyl-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-yl)-amine

Participants

Reaction Conditions

Reaction Steps

4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (100 mg, 0.48 mmol), aniline (0.13 mL, 1.44 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (23 mg, 0.05 mmol), and KOH (162 mg, 2.89 mmol) were dissolved in tert-butanol (2.0 mL), and stirred overnight at 100° C. The reaction mixture diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude material was triturated with EtOAc, filtered, washed with EtOAc, and dried under vacuum to provide 3 (63 mg, 50% yield) as a tan solid. LC-MS (M+H=265, obsd.=265).

Provenance & Evidence