Iodine → 2-Boc-Amino-3-iodo-4-chloropyridine

https://huagongshe.com/reaction/919298

Participants

Role	Name	HCID	Charge
Reactant	Iodine	HCID 807	—
Reactant	N,N,N',N'-Tetramethylethylenediamine	HCID 8037	—
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	tert-butyl N-(4-chloropyridin-2-yl)carbamate	HCID 1516418	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-Boc-Amino-3-iodo-4-chloropyridine	HCID 59852886	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

To a solution tert-butyl 4-chloropyridin-2-ylcarbamate (2.29 g, 10 mmol), TMEDA (2.32 g, 20 mmol) in anhydrous THF (30 mL) was added n-BuLi (8 ml, 20 mmol). The resulting mixture was allowed to stir at −78° C. for 0.5 h which was added the solution of I2 (2.54 g, 10 mmol) in THF (8 mL) dropwise at −78° C. The reaction mixture was stirred for another 4 h. To the solution was added NH4Cl aq (5 mL), extracted with EtOAc (3×20 mL), dried over Na2SO4, filtered and concentrated. The crude residue was purified by column chromatography to afford the title compound as a yellow solid. LC/MS m/z=355.19 [M+H]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09273033B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-8c646788ac8f46708e34e70700143ef5
Source note	uspto-grants-2016_03