methyl 6-amino-3,5-dibromopicolinate Chemical Properties

Boiling point:

366.0±37.0 °C(Predicted)

Density 

1.997

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

-0.94±0.10(Predicted)

Appearance

Light yellow to yellow Solid

methyl 6-amino-3,5-dibromopicolinate Usage And Synthesis

Uses

Methyl 6-Amino-3,5-dibromopyridine-2-carboxylate is used as a reagent in the synthesis of imidazopyridines as Syk inhibitors. Also used as a reagent in the synthesis of quinoline, quinoxaline and naphthyridine derivatives as antibacterial agents.

Synthesis

General procedure for the synthesis of methyl 6-amino-3,5-dibromopyridine-2-carboxylate, methyl 6-amino-3-bromopyridine-2-carboxylate, and methyl 5-bromo-6-aminopyridine-2-carboxylate from methyl 6-aminopyridine-2-carboxylate: over a period of 30 min, a solution of chloroform (40 mL) with bromine (2.57 mL) was added slowly and dropwise to methyl 6-aminopyridine-2-carboxylate ( 6.92 g) in a solution of chloroform (300 mL). The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the mixture was upsampled onto a silica gel column and purified by column chromatography (SiO2, heptane/ethyl acetate) to isolate three products: methyl 6-amino-5-bromo-pyridine-2-carboxylate (2 g, 19% yield), methyl 6-amino-3-bromo-pyridine-2-carboxylate (3 g, 29% yield) and methyl 6-amino-3,5-dibromopyridine-2-carboxylate (2.6 g, 18% yield).The 1H NMR (400 MHz, chloroform-d) data for methyl 6-amino-5-bromopyridine-2-carboxylate were as follows: δ 3.97 (s, 3H), 5.22 (br.s, 2H), 7.38 (d, J = 7.8 Hz, 1H), 7.79 (d, J = 7.8 Hz, 1H).

References

[1] Patent: WO2011/75591, 2011, A1. Location in patent: Page/Page column 95
[2] Patent: US2011/152312, 2011, A1. Location in patent: Page/Page column 40

methyl 6-amino-3,5-dibromopicolinate(443956-21-6)Related Product Information

• 6-amino-5-hydroxy-3-Pyridinecarboxylic acid methyl ester
• 2-Amino-3-bromopyrazine-5-carboxylic Acid
• 2-Pyridinecarboxylic acid, 6-broMo-5-Methoxy-, Methyl ester
• Methyl 3-broMo-6-chloropyrazine-2-carboxylate
• 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
• 3-AMINO-6-IODOPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
• Methyl 4,6-dihydroxypyridazine-3-carboxylate
• Methyl 5,6-dichloropicolinate
• METHYL-5-BROMOMETHYLPYRIDINE-2-CARBOXYLATE
• Methyl-5-(bromomethyl)pyrazine-2-carboxylate