2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → (R)-tert-butyl(1-(5-((6-(3,5-dichloro-4-hydroxyphenyl)-3-propionyl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol	HCID 66715127	—
Reactant	(R)-tert-butyl (1-(5-((6-chloro-3-propionyl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamate	HCID 117798298	—
Product	(R)-tert-butyl(1-(5-((6-(3,5-dichloro-4-hydroxyphenyl)-3-propionyl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamate	HCID 136981883	46.1%

Reaction Steps

Following general procedure II, (R)-tert-butyl(1-(5-((6-chloro-3-propionyl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamate (175 mg, 0.34 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (149 mg, 0.51 mmol) to afford the desired product (100 mg, 46%) as a solid: ESI MS m/z 637 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09067937B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-4cb1a492628a4d02a240075c7fd4b729
Source note	uspto-grants-2015_06