2-(Tributylstannyl)pyridine → (1H-Indol-5-yl)-(2-pyridin-2-yl-thieno[3,2-b]pyridin-7-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	2-(Tributylstannyl)pyridine	HCID 607784	—
Reactant	(2-bromo-thieno[3,2-b]pyridin-7-yl)-(1H-indol-5-yl)-amine	HCID 18382766	—
Catalyst	Copper iodide	HCID 83717	—
Catalyst	Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)	HCID 11007180	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(1H-Indol-5-yl)-(2-pyridin-2-yl-thieno[3,2-b]pyridin-7-yl)-amine	HCID 18382982	30.5%

Reaction Conditions

Temperature	90 °C

Reaction Steps

In a sealed tube (2-bromo-thieno[3,2-b]pyridin-7-yl)-(1H-indol-5-yl)-amine (150 mg, 0.29 mmol) and 2-(tributylstannyl)pyridine (118 mg, 1.1 mmol) were combined in 3 mL of dimethylformamide along with copper iodide (3 mg, 0.015 mmol). Nitrogen was bubbled through the solution and trans-benzyl(chloro)bis-(triphenylphosphine)palladium(II) (33 mg, 0.044 mmol) was added, the tube was sealed and heated to 90° C. After 14 hours the solution was cooled and concentrated to dryness. Chromatography on 15 g of silica gel with CH2Cl2/MeOH (5-20%) afforded 30.3 mg (28%) of,the title compound. LC-MS: 343 (MH+); HPLC RT: 3.94 minutes.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06492383B1
Source dataset	uspto-grants-2002_12
ORD ID	ord-d5c9c266044a481bbedc84023dda0685
Source note	uspto-grants-2002_12