ChemicalBook CAS DataBase List 2-Amino-4-bromopyridine

2-Amino-4-bromopyridine synthesis

11synthesis methods

Product Name:2-Amino-4-bromopyridine
CAS Number:84249-14-9
Molecular formula:C5H5BrN2
Molecular Weight:173.01

2-Amino-4-bromopyridine can be used as organic intermediate and pharmaceutical intermediate, mainly in laboratory research and development process. It can be synthesized by 4-bromopyridine hydrochloride through esterification, amination and Hoffmann degradation.

207799-10-8 Synthesis

207799-10-8
139 suppliers
$11.00/250mg

84249-14-9
369 suppliers
$6.00/1g

Yield:84249-14-9 58%

Reaction Conditions:

Stage #1:(4-bromopyridin-2-yl)-carbamic acid tert-butyl ester with water;hydrogen bromide for 16 h;
Stage #2: with water;sodium hydrogencarbonate

Steps:

2-Amino-4-bromopyridine (166)tert-Bxxy carbamate 155 (200 mg, 0.73 mol) is suspended in water (1 mL) and treated with HBr (1 mL, 48 wt. % in water). After stirring 16 h, the reaction mixture is poured onto aqueous NaHCO₃ (25 mL) and extracted into EtOAc (3 x 25 mL). The combined EtOAc phases are dried (MgSO₄) and reduced in vacuo. The title compound is obtained after chromatography of this residue (neat EtOAc).Yield: 73 mg (58%).LC/MS t_x 0.69 min.MS(ES+) m/z 175, 173 (M+H).

References:

CURIS, INC. WO2008/57497, 2008, A2 Location in patent:Page/Page column 301

FullText