2-BROMO-5-AMINO-4-PICOLINE Chemical Properties

Boiling point:

306.9±37.0 °C(Predicted)

Density 

1.593±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.38±0.18(Predicted)

form 

Powder

color 

Brown

CAS DataBase Reference

156118-16-0

Safety Information

RIDADR 

UN2811

HazardClass 

6.1

HS Code 

2933399990

2-BROMO-5-AMINO-4-PICOLINE Usage And Synthesis

Synthesis

A suspension of 2-bromo-4-methyl-5-nitropyridine (XIV) (200 g, 921 mmol, 1.00 eq.) was formed with NH4Cl (240 g, 4.49 mol, 4.87 eq.) in EtOH (3.50 L) and water (150 mL). The mixture was heated to 50 °C with stirring. Subsequently, Fe (120 g, 2.15 mol, 2.33 eq.) and HCl (10.2 g, 279 mmol, 0.30 eq.) were added to the mixture. The suspension was heated to 80 °C and kept for 3 hours. After completion of the reaction, the mixture was cooled to 25 °C and filtered through a diatomaceous earth plug. The filtrate was concentrated under reduced pressure to give a residue. The residue was dissolved in EtOAc (1L x 3) and washed with brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-4-methylpyridin-3-amine (XV) as a brown solid (167.9 g, 898 mmol, 97.4% yield), which could be used for the next reaction without further purification.1H NMR (CDCl3,400 MHz) δ ppm 2.15 (s, 3H), 3.44 (br s 2H), 7.14 (s, 1H), 7.78 (s, 1H); ESIMS m/z 186.8 ([M + H]+).

References

[1] Patent: WO2017/23975, 2017, A1. Location in patent: Paragraph 0610; 0611
[2] Patent: WO2017/24026, 2017, A1. Location in patent: Paragraph 0614; 0615
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3441 - 3446
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5258 - 5264
[5] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 6, p. 2441 - 2452

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