Tetrahydrofuran → 4-Benzo[b]thiophen-7-yl-2-fluoro-5-methyl-pyridine

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Fluoro-4-iodo-5-methylpyridine	HCID 10060052	—
Reactant	2-(Benzo[b]thiophen-7-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 66673976	—
Catalyst	2-(Di-tert-butylphosphino)biphenyl	HCID 2734215	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Chloroform isopropyl alcohol	HCID 21906603	—
Product	4-Benzo[b]thiophen-7-yl-2-fluoro-5-methyl-pyridine	HCID 66674047	82.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

In a flask, combine 2-fluoro-4-iodo-5-methyl-pyridine (355 mg, 1.5 mmol), 2-benzo[b]thiophen-7-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (282 mg, 1.8 mmol), Pd(dppf)Cl2 (61 mg, 0.07 mmol), 2-(di-tert-butylphos-phino)biphenyl (13 mg, 0.04 mmol), sodium carbonate (2 M, 1.5 mL, 3 mmol) and THF (10 mL). Heat the mixture at 100° C. for 3 h in an oil bath. Dilute the mixture with chloroform/IPA (3/1). Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate in vacuo to a dark residue. Purify by column chromatography (20% ethyl acetate in hexane) to afford the title compound (300 mg, 82%) as a yellow oil. MS (ES) m/z 244 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08114872B2
Source dataset	uspto-grants-2012_02
ORD ID	ord-babefff2256742279d84c585fac63b71
Source note	uspto-grants-2012_02