Potassium Hydroxide → HCID 58167971, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine	HCID 11459088	—
Reactant	1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one	HCID 58168008	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Methanol	HCID 887	—
Solvent	2-Methyl-2-butanol	HCID 6405	—
Product	HCID 58167971	HCID 58167971	2.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Compound 83 (100 mg, 0.43 mmol), 3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamine (156 mg, 0.65 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (21 mg, 0.04 mmol), and KOH (97 mg, 1.73 mmol) were suspended in tert-amyl alcohol (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered, and purified via prep-LC-MS to provide 156 (4 mg, 2% yield) as a solid. LC-MS (M+H=434, obsd.=434).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-d7665df0868446e4b325cdb7e09e8f68
Source note	uspto-grants-2014_05