Dichloromethane → 2-Bromo-6-cyclobutylpyridine

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	2,6-Dibromopyridine	HCID 12274	—
Reactant	HCID 178419766	HCID 178419766	—
Catalyst	Copper iodide	HCID 83717	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-Bromo-6-cyclobutylpyridine	HCID 45788026	55%

Reaction Steps

A round bottom flask was charged with dry THF (50 mL), 2,6-dibromopyridine (3.00 g, 12.7 mmol), copper iodide (0.555 g, 2.91 mmol) and PdCl2(dppf):dichloromethane adduct (1.09 g, 1.33 mmol). The mixture was purged with argon for 10 minutes, and then cyclobutyl zinc bromide (0.5 M in THF, 30.4 mL, 15.2 mmol) was added and the mixture stirred at ambient temperature for 2 hours. The mixture was quenched with saturated ammonium chloride solution and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (5% ethyl acetate/hexane) afforded 1.48 g (55%) of the title compound as an orange oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09174981B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-d590e15c9cf74dc1b243ec44b72edbeb
Source note	uspto-grants-2015_11