Potassium Carbonate → 2-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-4-methyl-oxazole-5-carboxylic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Ethyl 2-bromo-4-methyl-1,3-oxazole-5-carboxylate	HCID 12785854	—
Reactant	2-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate	HCID 58016204	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	2-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-4-methyl-oxazole-5-carboxylic acid ethyl ester	HCID 71008482	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

Under N2, acetic acid 2-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (preparation described in intermediate-4, 72 mg, 0.153 mmol), 2-bromo-4-methyl-oxazole-5-carboxylic acid ethyl ester (34 mg, 0.146 mmol), Pd(dppf)Cl2 (36 mg, 0.0438 mmol) and K2CO3 (61 mg, 0.438 mmol) were dissolved in dioxane/H2O (5:1, 6 mL). The reaction mixture was stirred at 100° C. for about 1.5 h. The solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=2:1) to give 2-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-4-methyl-oxazole-5-carboxylic acid ethyl ester.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08729078B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-2f3313be377c49d7b3c10aa8861be017
Source note	uspto-grants-2014_05