Sodium Acetate → [4-(5-Cyclobutaneamido-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetate

https://huagongshe.com/reaction/520297

Participants

Role	Name	HCID	Charge
Reactant	Sodium Acetate	HCID 517045	—
Reactant	[4-(Dihydroxyboranyl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetate	HCID 86684340	—
Reactant	N-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)cyclobutanecarboxamide	HCID 117777382	—
Catalyst	Water	HCID 962	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Acetonitrile	HCID 6342	—
Product	[4-(5-Cyclobutaneamido-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetate	HCID 117777446	56%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 101a (230 mg, 0.80 mmol), {3-[(acetyloxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic acid (320 mg, 0.80 mmol), Pd(dppf)Cl2 (42 mg, 0.050 mmol), NaOAc (82 mg, 1.0 mmol), K3PO4.3H2O (266 mg, 1.0 mmol), water (5 drops) and acetonitrile (6 mL). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 1 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica-gel column chromatography eluting with 20:1 dichloromethane/methanol to afford 101b (200 mg, 56%) as a brown solid. MS-ESI: [M+H]+ 558.3

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09326985B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-f4568fb9cc3743dea3a9c5618877e6b6
Source note	uspto-grants-2016_05