Potassium Hydroxide → N-[4-(6,7,8,9-Tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-ylamino)-phenyl]-benzamide

https://huagongshe.com/en/reaction/533721

Participants

Role	Name	HCID	Charge
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	Benzamide, N-(4-aminophenyl)-	HCID 87196	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrole	HCID 66677972	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	tert-Butanol	HCID 6386	—
Product	N-[4-(6,7,8,9-Tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-ylamino)-phenyl]-benzamide	HCID 46843080	37.4%

Reaction Conditions

Temperature	100 °C

Reaction Steps

4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (500 mg, 1.78 mmol), N-(4-Amino-phenyl)-benzamide (454 mg, 2.14 mmol), Pd(OAc)2 (20 mg, 0.09 mmol), X-Phos (85 mg, 0.18 mmol), and KOH (300 mg, 5.35 mmol) were dissolved in tert-butanol (9.0 mL), and stirred overnight at 100° C. The reaction mixture was concentrated, and then suspended in EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 1 (255 mg, 37% yield) as a tan solid. LC-MS (M+H=384, obsd.=384).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853391B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-3499e09f59414261905778bb3ef10ebb
Source note	uspto-grants-2014_10