2-Amino-3-Difluoromethoxy-5-Bromopyridine Chemical Properties

Boiling point:

248.9±35.0 °C(Predicted)

Density 

1.752

storage temp. 

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

pka

4.85±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2933399990

2-Amino-3-Difluoromethoxy-5-Bromopyridine Usage And Synthesis

Uses

5-Bromo-3-(Difluoromethoxy)Pyridin-2-Amine is used in preparation of imidazo[1,2-a]pyridinyl derivatives and their use in the treatment of disease.

Synthesis

General procedure for the synthesis of 2-amino-3-(difluoromethoxy)-5-bromopyridine from 3-(difluoromethoxy)pyridin-2-amine: N-bromosuccinimide (2.61 g, 14.65 mmol) was slowly added to an acetonitrile solution (15 mL) of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) over a period of 3 min at 0 °C ) in acetonitrile. The reaction mixture was continued to be stirred at the same temperature for 20 minutes. Subsequently, the reaction solution was concentrated to dryness in vacuo and the resulting viscous material was diluted with water and extracted with ethyl acetate (3 x 60 mL). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated again to dryness. The residue was purified by column chromatography (silica gel, 100-200 mesh, 20% hexane solution of ethyl acetate as eluent) to afford the target product 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 93% yield). The product was confirmed by NMR hydrogen spectrum (400 MHz, DMSO-d6): δ 7.89 (s, 1H), 7.51 (s, 1H), 7.16 (t, J = 73.6 Hz, 1H), 6.34 (s, 2H).

References

[1] Patent: WO2014/111496, 2014, A1. Location in patent: Page/Page column 108; 109
[2] Patent: WO2015/91889, 2015, A1. Location in patent: Page/Page column 74, 75
[3] Patent: US2015/175619, 2015, A1. Location in patent: Paragraph 0221; 0222
[4] Patent: WO2009/16460, 2009, A2. Location in patent: Page/Page column 56
[5] Patent: US2013/210818, 2013, A1. Location in patent: Paragraph 0416

2-Amino-3-Difluoromethoxy-5-Bromopyridine(947249-13-0)Related Product Information

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