Potassium Carbonate → N,N-Dimethyl-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,N-Dimethylsulphonamido)benzeneboronic acid	HCID 44119328	—
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,N-Dimethyl-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yl)-benzenesulfonamide	HCID 58168133	73.5%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Compound 83 (100 mg, 0.43 mmol), 4-(N,N-dimethylsulfonamidophenyl)boronic acid (198 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. The resulting precipitate was filtered, washed with H2O/EtOAc, and dried under vacuum to provide 171 (120 mg, 73% yield) as a grey solid. LC-MS (M+H=380, obsd.=380).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-e3e223b43df645e59acb24c10f8d08d9
Source note	uspto-grants-2014_05