Styrylboronic acid → HCID 118324017, compound

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	HCID 118324025	HCID 118324025	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 118324017	HCID 118324017	—

Reaction Conditions

Temperature	35 °C

Reaction Steps

A mixture of (4-bromo-2-(tert-butoxy)quinolin-6-yl)(4-chlorophenyl)(4-methoxyphenyl)methanol (107 mg, 0.203 mmol), (E)-styrylboronic acid (60 mg, 0.406 mmol), Pd(OAc)2 (4.56 mg, 0.0203 mmol), SPhos (16.7 mg, 0.0406 mmol) and K3PO4.H2O (86.2 mg, 0.406 mmol) in anhydrous THF (1 mL) was heated at 35° C. overnight. The reaction was diluted with DCM and water. The organics were washed with water and concentrated. The crude material was purified by silica column (40-55% EtOAc/hexanes) to yield (E)-(2-(tert-butoxy)-4-styrylquinolin-6-yl)(4-chlorophenyl)(4-methoxyphenyl)methanol.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09266835B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-e62a96e737f24300b1695bfe1f71e749
Source note	uspto-grants-2016_02