Potassium Phosphate, Tribasic → [4-(5-{[6-(2-{[(Tert-butoxy)carbonyl]amino}ethoxy)pyridin-2-yl]amino}-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

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
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	Tert-butyl 2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethylcarbamate	HCID 118116413	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Acetonitrile--water (1/1)	HCID 18373917	—
Product	[4-(5-{[6-(2-{[(Tert-butoxy)carbonyl]amino}ethoxy)pyridin-2-yl]amino}-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 118117153	50%

Reaction Conditions

Temperature	95 °C

Reaction Steps

A 50 mL round-bottomed flask equipped with a reflux condenser was charged with 101b (500 mg, 1.14 mmol), [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 101c (452 mg, 1.14 mmol), K3PO4 (483 mg, 2.28 mmol), NaOAc (187 mg, 2.28 mmol), Pd(dppf)Cl2 (42 mg, 0.057 mmol), and CH3CN/H2O (20.0/0.5 mL). The system was subject to three cycles of vacuum/argon flush then heated at 95° C. under N2 for 1 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica-gel column-chromatography eluting with DCM/MeOH (70:1 to 30:1) to afford 101d (400 mg, 50%) as yellow solid. MS-ESI: [M+H]+ 712.3

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09260415B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-0d063457200d42fdbe29b1bb7960c20d
Source note	uspto-grants-2016_02