Potassium Carbonate → HCID 58168268, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(3-Methoxyphenyl)boronic acid	HCID 2734370	—
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 58168268	HCID 58168268	17%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Compound 83 (50 mg, 0.22 mmol), 3-methoxyphenylboronic acid (49 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. The crude product was purified directly via Biotage eluting with a gradient of 25 to 85% EtOAc in hexanes to provide 152 (11 mg, 17% yield) as a white solid. LC-MS (M+H=303, obsd.=303).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08735584B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-bf9900f0294440a1979c4245326611fd
Source note	uspto-grants-2014_05