3,5-Dibromopyridine → 2-(5-Bromo-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	3,5-Dibromopyridine	HCID 69369	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	1-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)	HCID 2773302	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-(5-Bromo-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester	HCID 117667444	24.5%

Reaction Conditions

Temperature	80 °C

Reaction Steps

1-(tert-Butoxycarbonyl)indole-2-boronic acid (900 mg, 3.5 mmol), 3,5-dibromo-pyridine (810 mg, 3.5 mmol), KOAc (1.01 g, 10.4 mmol) and Pd(dppf)Cl2 (252 mg, 0.35 mmol) are mixed in 1,4-dioxane (70 mL) and heated to 80° C. for 2 hours. The mixture is filtered and the filtrate is concentrated. The residue is dissolved in DCM and washed with water. The organic layer is separated, dried over Na2SO4, filtered and concentrated to afford the crude product which is purified by column chromatography to give 320 mg of 2-(5-bromo-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181272B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-8ff11408cbda479188f4a9423fed6c83
Source note	uspto-grants-2015_11