Ethyl 2-aminobenzoate → Ethyl acetate hexane

https://huagongshe.com/reaction/42070

Participants

Role	Name	HCID	Charge
Reactant	Ethyl 2-aminobenzoate	HCID 6877	—
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	5-Bromo-2-(3-methoxyphenyl)pyridine	HCID 49758519	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	Ethyl acetate hexane	HCID 21226206	98.4%
Product	2-(6-(3-Methoxyphenyl)pyridin-3-ylamino)benzoic acid	HCID 25186999	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

In a schlenck tube, a mixture of 5-bromo-2-(3-methoxyphenyl)pyridine (Intermediate 27, 0.91 mmol, 0.23 g), ethyl 2-aminobenzoate (Intermediate 33, 0.91 mmol, 0.15 g), BINAP (0.05 mmol, 0.028 g), Pd2(dba)3 (0.05 mmol, 0.042 g) and NaOtBu (1.82 mmol, 0.175 g) in toluene (4 ml) was heated at 110° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the solid residue was triturated with aqueous solution of 2N HCl and extracted with CHCl3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.078 g (yield 26%) of the expected compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536165B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-0c6010783c884be28f919b4217d37301
Source note	uspto-grants-2013_09