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	96.8%

Reaction Conditions

Temperature	65 °C

Reaction Steps

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 116b (1.0 g, 2.5 mmol), Pin2B2 (3.2 g, 12.5 mmol), Pd(dppf)Cl2 (75 mg, 0.125 mmol), X-phos (75 mg, 0.25 mmol), potassium acetate (750 mg, 7.5 mmol), and dioxane (60 mL). After three cycles of vacuum/argon flush, the mixture was heated at 65° C. for 15 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was washed with 3:1 petroleum ether/ethyl acetate (10 mL) to afford 116c as yellow solid (1.0 g, LCMS purity: 75%). MS: [M+H]+ 414.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08754077B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-011552214ef84000b0be1ee67a4beb64
Source note	uspto-grants-2014_06