2-AMINO-6-BROMOPYRIDIN-3-OL Chemical Properties

Boiling point:

421.3±45.0 °C(Predicted)

Density 

1.898

storage temp. 

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

pka

4.59±0.23(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C5H5BrN2O/c6-4-2-1-3(9)5(7)8-4/h1-2,9H,(H2,7,8)

InChIKey

JSRWVRYNUHTJOL-UHFFFAOYSA-N

SMILES

C1(N)=NC(Br)=CC=C1O

2-AMINO-6-BROMOPYRIDIN-3-OL Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-6-bromopyridin-3-ol from 6-bromo-2-nitropyridin-3-ol: 6-bromo-2-nitropyridin-3-ol (3 g, 13.7 mmol), iron powder (7657.88 mg, 136.99 mmol) and ammonium chloride (7329.1 mg, 136.99 mmol) were reacted with stirring at 75°C for 2 hours in a mixture of ethanol (100 mL) and water (100 mL) in a solvent mixture of ethanol (100 mL) and water, and the reaction was stirred at 75 °C for 2 h. The reaction mixture turned into a black suspension. After completion of the reaction, the mixture was cooled to room temperature and filtered through diatomaceous earth to remove insoluble impurities. The filtrate was concentrated under reduced pressure to afford the crude product 2-amino-6-bromopyridin-3-ol (2.5 g, 13.22 mmol, 96.55% yield) as a solid. The structure of the product was confirmed by 1H NMR (DMSO-d6, 400 MHz): δH= 9.71 (s, 1H), 6.74 (d, 1H), 6.50 (d, 1H), 5.92 (br s, 2H).

References

[1] Patent: WO2018/148745, 2018, A1. Location in patent: Page/Page column 163
[2] Patent: CN107188900, 2017, A. Location in patent: Paragraph 0039; 0042; 0043
[3] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 255 - 266
[4] Patent: WO2018/93569, 2018, A1. Location in patent: Page/Page column 198; 199
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1222 - 1237

2-AMINO-6-BROMOPYRIDIN-3-OL(934758-27-7)Related Product Information

• 6-Bromo-3-methoxy-2-nitro-pyridine
• 6-BROMO-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
• 6-BROMO-3,4-DIHYDRO-2H-PYRIDO[3,2-B][1,4]OXAZINE
• 6-Bromo-2-nitro-pyridin-3-ol
• 2-AMINO-6-BROMOPYRIDIN-3-OL