Dichloromethane → 4-Benzo[b]thiophen-7-yl-2-chloro-pyridine

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Chloropyridine-4-boronic acid, pinacol ester	HCID 5103408	—
Reactant	7-Bromobenzo[b]thiophene	HCID 12045538	—
Catalyst	2-(Di-tert-butylphosphino)biphenyl	HCID 2734215	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Chloroform isopropyl alcohol	HCID 21906603	—
Product	4-Benzo[b]thiophen-7-yl-2-chloro-pyridine	HCID 86640254	66.3%

Reaction Conditions

Temperature	100 °C

Reaction Steps

In a flask, combine 7-bromo-benzo[b]thiophene (1.7 g, 12 mmol), 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.6 g, 7 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (285 mg, 0.3 mmol), 2-(di-tert-butylphosphino)biphenyl (63 mg, 0.2 mmol), sodium carbonate (2 M, 8 mL, 16 mmol) and THF (20 mL). Heat the mixture at 100° C. for 3 hours. Dilute the mixture with chloroform/isopropanol (3/1). Wash the solution with saturated aqueous sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo to a dark residue. Purify by column chromatography (dichloromethane to 20% THF in dichloromethane) to afford the title compound (1.14 g, 66%) as a yellow solid. MS (ES) m/z 246 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08101628B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-50a336f664f14e72bf0fed21c70efb66
Source note	uspto-grants-2012_01