Methyl 2-amino-5-bromo-4-pyridinecarboxylate Chemical Properties

Boiling point:

311.5±37.0 °C(Predicted)

Density 

1.662±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.78±0.24(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C7H7BrN2O2/c1-12-7(11)4-2-6(9)10-3-5(4)8/h2-3H,1H3,(H2,9,10)

InChIKey

FJPDYKLTAURVRU-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C(C(OC)=O)=C1

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

Methyl 2-amino-5-bromo-4-pyridinecarboxylate Usage And Synthesis

Uses

Methyl 2-amino-5-bromo-4-pyridinecarboxylate is a halogenated derivative of pyridinecarboxylate. It is a crucial compound that could be used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

Step 15.1: Synthesis of methyl 2-amino-5-bromoisonicotinate. Methyl 2-aminoisonicotinate (5.58 g, 36.7 mmol) was dissolved in DMF (56 mL) and cooled to -18°C (using an ice/MeOH bath). At -18 °C, N-bromosuccinimide (NBS, 7.21 g, 38.5 mmol) was added to the reaction mixture in batches and stirred for 1 h at the same temperature. After completion of the reaction, the mixture was diluted with ethyl acetate (AcOEt, 500 mL) and washed with water (2 x 250 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product methyl 2-amino-5-bromoisonicotinate (3.0 g, 13.0 mmol, 35% yield) as a yellow solid, which was used directly in the next reaction without further purification. Mass spectrometry (MS): m/z 231 [M + H]+; high performance liquid chromatography (HPLC): retention time (Rt) = 0.70 min.

References

[1] Patent: WO2007/113226, 2007, A1. Location in patent: Page/Page column 126-127
[2] Patent: US2006/84802, 2006, A1. Location in patent: Page/Page column 29

Methyl 2-amino-5-bromo-4-pyridinecarboxylate(882499-87-8)Related Product Information

• Methyl nicotinate
• Methyl isonicotinate
• 2-Amino-5-bromopyridine
• 2-Amino-5-bromoisonicotinic acid
• 3-BROMOISONICOTINIC ACID METHYL ESTER
• METHYL 2-AMINO-5-BROMO-4-PYRIDINECARBOXYLATE
• 3-Bromoisonicotinic acid
• Methyl 2-aminopyridine-4-carboxylate