Tricyclohexylphosphine → (5-(1-Vinylcyclopropyl)pyridin-3-yl)boronic acid

Participants

Role	Name	HCID	Charge
Reactant	Tricyclohexylphosphine	HCID 75806	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	3-Bromo-5-(1-ethenylcyclopropyl)pyridine	HCID 89155903	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(5-(1-Vinylcyclopropyl)pyridin-3-yl)boronic acid	HCID 89961615	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A vial containing the title compound from Example 73 Step C (0.036 g, 0.161 mmol), bis(pinacolato)diboron (0.082 g, 0.321 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.029 g, 0.032 mmol), tricyclohexylphosphine (0.018 g, 0.064 mmol) and potassium acetate (0.047 g, 0.48 mmol) in dioxane (0.80 mL) was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction was then passed through a syringe filter and concentrated under reduced pressure to provide the title compound: LCMS m/z 189.12 [M]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09073929B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-5031391e519c4ba2ab2871b5b953f2e1
Source note	uspto-grants-2015_07