2(3H)-Benzoxazolone → HCID 59627760, compound

Participants

Role	Name	HCID	Charge
Reactant	2(3H)-Benzoxazolone	HCID 6043	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1-N,2-N-dimethylcyclohexane-1,2-diamine	HCID 551074	—
Reactant	5-Iodo-4'-methyl-biphenyl-3-carboxylic acid methyl ester	HCID 57851588	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 59627760	HCID 59627760	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

5-Iodo-4′-methyl-biphenyl-3-carboxylic acid methyl ester (200 mg, 0.57 mmol) was dissolved in DMF (3 mL) and 2-benzoxazolinone (270 mg, 2.0 mmol), K3PO4 (424 mg, 2.0 mmol), CuI (15 mg), and 1,2-bis(methylamino)cyclohexane (0.15 mL) were added. The reaction mixture was stirred at 110° C. overnight, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified by preparative thin layer chromatography (3:1 hexanes/ethyl acetate) to give 4′-methyl-5-(2-oxo-benzooxazol-3-yl)-biphenyl-3-carboxylic acid methyl ester, which was used directly in the subsequent step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08809402B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-fd1e310359054e6b85c851e211997b80
Source note	uspto-grants-2014_08