1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → tert-butyl (1-(4-(8-(1,5-dimethyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 42647313	—
Reactant	tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate	HCID 86671031	—
Reactant	tert-butyl (1-(4-(4-oxo-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate	HCID 86671060	—
Product	tert-butyl (1-(4-(8-(1,5-dimethyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate	HCID 68227656	82%

Reaction Steps

Following the procedure used to prepare tert-butyl (1-(4-(4-oxo-2-phenyl-8-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate, tert-butyl (1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate was reacted with 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to give the title compound (46 mg, 82%). LCMS (Method I): RT=7.35 min, [M+H]+=563.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546376B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-5cc555e82f344faa85d18a08c0d8104a
Source note	uspto-grants-2013_10