Potassium Phosphate, Tribasic → HCID 22317976, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	5-Bromo-2-iodopyridine	HCID 593690	—
Reactant	4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane	HCID 10997426	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	HCID 22317976	HCID 22317976	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

5-Bromo-2-isopropenyl-pyridine was prepared according to the scheme shown in FIG. 9. In the sealed round bottom flask, 2-Iodo-5-bromopyridine (4.34 g, 15.3 mmol), isopropenylboronic acid pinacol ester (2.57 g, 15.3 mmol), PdCl2(dppf) (1.87 g, 2.3 mmol) and potassium phosphate (8.2 g, 38 mmol) were dissolved in 25 mL DME and 8 mL water. The resulting solution was stirred at 80° C. for 3 hours and was then cooled down to room temperature. After separation, the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After removing the solvent, fairly pure product (about 3.0 g) was obtained as yellow solid, which was directly used for next step without further purification. ESI MS m/z 198, 200 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07666864B2
Source dataset	uspto-grants-2010_02
ORD ID	ord-d235dfdfce544adf8ff6620ebe5ec44e
Source note	uspto-grants-2010_02