Styrylboronic acid → (Z)-(4-chlorophenyl)(4-styrylquinolin-6-yl)(thiazol-4-yl)methanol

Participants

Role	Name	HCID	Charge
Reactant	Styrylboronic acid	HCID 5702628	—
Reactant	2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl	HCID 11269872	—
Reactant	Potassium phosphate, tribasic, monohydrate	HCID 22031701	—
Reactant	(4-Chlorophenyl)(4-chloroquinolin-6-yl)(thiazol-4-yl)methanol	HCID 118324081	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(Z)-(4-chlorophenyl)(4-styrylquinolin-6-yl)(thiazol-4-yl)methanol	HCID 118324027	—

Reaction Conditions

Temperature	30 °C

Reaction Steps

A mixture of (4-chlorophenyl)(4-chloroquinolin-6-yl)(thiazol-4-yl)methanol (65 mg, 0.168 mmol), (E)-styrylboronic acid (39.74 mg, 0.269 mmol), Pd(OAc)2 (3.77 mg, 0.0168 mmol), SPhos (13.8 mg, 0.0336 mmol), and K3PO4.H2O (71.25 mg, 0.336 mmol) in anhydrous THF (1.5 mL) was stirred at 30° C. overnight. The reaction was diluted with EtOAc and water. The organics were concentrated and purified by REDSEP GOLD silica column (40% EtOAc/heptanes) to yield (Z)-(4-chlorophenyl)(4-styrylquinolin-6-yl)(thiazol-4-yl)methanol

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09266835B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-760cbe80442749c09cd93fe22c182fee
Source note	uspto-grants-2016_02