Potassium Carbonate → N-(2-Hydroxy-ethyl)-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yl)-benzenesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl	HCID 11269872	—
Reactant	(4-(N-(2-Hydroxyethyl)sulfamoyl)phenyl)boronic acid	HCID 44119332	—
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	—
Solvent	Water ethylacetate	HCID 22728543	—
Product	N-(2-Hydroxy-ethyl)-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yl)-benzenesulfonamide	HCID 69815493	4%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Compound 83 (100 mg, 0.43 mmol), 4-(2-hydroxyethylsulfamoyl)phenylboronic acid (212 mg, 0.87 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), S-Phos (18 mg, 0.04 mmol), and K2CO3 (299 mg, 2.17 mmol) were dissolved in dioxane/H2O (2.2 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was diluted with H2O/EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 10% MeOH in CH2Cl2. The resulting material was triturated with MeOH, filtered, and dried under vacuum to provide 174 (6 mg, 4% yield) as a light-yellow solid. LC-MS (M+H=396, obsd.=396).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-56f590d7ee3541859663f9c58e2073c2
Source note	uspto-grants-2014_05