Iodine → tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

https://huagongshe.com/reaction/1969174

Participants

Role	Name	HCID	Charge
Reactant	Iodine	HCID 807	—
Reactant	Water	HCID 962	—
Reactant	(6-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester	HCID 7330593	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate	HCID 53415320	32.3%

Reaction Conditions

Temperature	-78 °C

Reaction Steps

To the solution of tert-butyl (6-chloropyridin-3-yl)carbamate (160 g, 0.7 mol) in 1 L of anhydrous THF was added n-BuLi (600 mL, 1.5 mol) at −78° C. under N2 atmosphere. After the addition was finished, the solution was stirred at −78° C. for 30 min, and the solution of I2 (177.68 g, 0.7 mol) in 800 mL of anhydrous THF was added. Then the solution was stirred at −78° C. for 4 hrs. TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and purified by flash chromatography to afford 80 g of tert-butyl (6-chloro-4-iodopyridin-3-yl)carbamate as a yellow solid (32.3%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08426450B1
Source dataset	uspto-grants-2013_04
ORD ID	ord-5bf221f0b879467d8382c230603cb966
Source note	uspto-grants-2013_04