Potassium Acetate → 3-(Acetoxymethyl)-2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)pyridin-4-ylboronic Acid

Participants

Role	Name	HCID	Charge
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	(2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-chloropyridin-3-yl)methyl Acetate	HCID 86683941	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-(Acetoxymethyl)-2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)pyridin-4-ylboronic Acid	HCID 86683943	66%

Reaction Conditions

Temperature	65 °C

Reaction Steps

A mixture of 104b (150 mg, 0.37 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane), Pin2B2 (379 mg, 1.48 mmol), Pd(dppf)Cl2 (28 mg, 0.037 mmol), Xphos (35 mg, 0.074 mmol) and KOAc (108 mg, 1.11 mmol) in dioxane (5 mL) was stirred at 65° C. for 15 h under N2. The reaction mixture was concentrated. The residue was washed with DCM/PE (1 mL/20 mL) and filtered. The filtrate was concentrated to give 104c (100 mg, 66%) as yellow solid. MS-ESI: [M+H]+ 414.2

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09260415B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-dee7f1f91d9948b3b6031d38e9123649
Source note	uspto-grants-2016_02