4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane → HCID 86674277, compound

Participants

Role	Name	HCID	Charge
Reactant	4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane	HCID 10997426	—
Reactant	2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl	HCID 11269872	—
Reactant	Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate	HCID 86674246	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 86674277	HCID 86674277	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate (180 mg, 0.50 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (126 mg, 0.75 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), S-PHOS (41 mg, 0.10) K3PO3 (318 mg, 1.50 mmol) were dissolved in toluene (2 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748624B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-9febdb8389db48369f7d514183d6033b
Source note	uspto-grants-2014_06