Ethyl pyridine-4-acetate → 3-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Ethyl pyridine-4-acetate	HCID 736321	—
Reactant	Sodium bis(trimethylsilyl)amide	HCID 2724254	—
Reactant	8-{3-[Chloro-(4-chloro-phenyl)-methyl]-phenyl}-6-isopropyl-quinoline	HCID 22350110	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	Ammonium Chloride	HCID 25517	—
Solvent	tetrahydrofuran HMPA	HCID 86583969	—
Product	3-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester	HCID 20814966	—

Reaction Conditions

Temperature	21 °C

Reaction Steps

To a solution of ethyl 4-pyridinylacetate (1.28 g, 7.74 mmol) in THF/HMPA (3:1, 5 mL) at −10° C. was added NaHMDS (1M, 7.8 mL, 7.8 mmol) dropwise. After 60 min., the crude chloride from Step 2 above was added and the resulting reaction mixture was stirred for 18 h at 21° C., and then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06919353B2
Source dataset	uspto-grants-2005_07
ORD ID	ord-d6d57069dc714e23b79b60f542161d26
Source note	uspto-grants-2005_07