3-amino-5-bromopyridine-2-carboxylic acid Chemical Properties

Melting point:

>170°C (dec.)

Boiling point:

399.0±42.0 °C(Predicted)

Density 

1.909±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.15±0.10(Predicted)

color 

Yellow

InChI

InChI=1S/C6H5BrN2O2/c7-3-1-4(8)5(6(10)11)9-2-3/h1-2H,8H2,(H,10,11)

InChIKey

GXXIHPZAIYKHGG-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=C(Br)C=C1N

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

3-amino-5-bromopyridine-2-carboxylic acid Usage And Synthesis

Uses

3-amino-5-bromopyridine-2-carboxylic acid is used in the preparation of biological reagents such as macrocyclic glucagon-like peptide 1 receptor agonists. It is also used in the preparation of pyridinamide and indoline compounds.

Synthesis

Step 2: Synthesis of 3-amino-5-bromopyridine-2-carboxylic acid To a 100 mL round bottom flask was added 3-amino-5-bromopyridine-2-carboxamide (1.05 g, 4.9 mmol) and aqueous sodium hydroxide solution (0.98 g dissolved in 10 mL of water, 24.5 mmol). The reaction mixture was heated to reflux temperature and stirred for 5 hours. Upon completion of the reaction, volatiles were removed by distillation under reduced pressure to give a residue. The residue was neutralized with 2N HCl at 0 °C to pH=7.0 and precipitate was precipitated. The precipitate was collected by filtration and dried to give 3-amino-5-bromopyridine-2-carboxylic acid as a light yellow solid (1 g, 95% yield). 1H NMR (300 MHz, DMSO-d6): δ 7.65 (d, J=2.1 Hz, 1H), 7.20 (d, J=2.1 Hz, 1H), 7.01-7.16 (br s, 2H). LC-MS (ESI): calculated: 215.9; measured: 217.0 [M+H]+ (RT: 0.43 min).

References

[1] Patent: WO2012/58671, 2012, A1. Location in patent: Page/Page column 117-118
[2] Patent: US2014/38952, 2014, A1. Location in patent: Page/Page column 0180-0181
[3] Patent: EP1757594, 2007, A1. Location in patent: Page/Page column 77
[4] Patent: WO2008/76425, 2008, A1. Location in patent: Page/Page column 33
[5] Patent: WO2008/130600, 2008, A2. Location in patent: Page/Page column 56

3-amino-5-bromopyridine-2-carboxylic acid(870997-85-6)Related Product Information

• 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE
• 5-BROMO-3-NITROPYRIDINE-2-CARBOXYLIC ACID
• ethyl 3-amino-5-bromopyridine-2-carboxylate
• 5-Bromopicolinic acid
• 3-amino-5-bromopyridine-2-carboxylic acid
• 3-Amino-2-pyridinecarboxylic acid