Potassium Carbonate → HCID 58168004, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Fluorophenylboronic acid	HCID 2734354	—
Reactant	2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl	HCID 11269872	—
Reactant	1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one	HCID 58168008	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	HCID 58168004	HCID 58168004	10%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Compound 83 (50 mg, 0.22 mmol), 2-fluorophenylboronic acid (46 mg, 0.33 mmol), Pd(OAc)2 (2 mg, 0.01 mmol), S-Phos (9 mg, 0.02 mmol), and K2CO3 (90 mg, 0.65 mmol) were dissolved in dioxane/H2O (2.2 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, diluted with MeOH/DMSO, and filtered. The filtrate was purified via prep-LC-MS. The product was triturated with MeOH, filtered, and dried under vacuum to provide 153 (6 mg, 10% yield) as a white solid. LC-MS (M+H=291, obsd.=291).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-77f10048c6534417a443da4fc2fc3fad
Source note	uspto-grants-2014_05