(2-BROMO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

84-85°C

Boiling point:

298.9±25.0 °C(Predicted)

Density 

1.453±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

12.00±0.70(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

(2-BROMO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Chemical Properties

White solid

Synthesis

Step 1: Synthesis of tert-butyl 2-bromopyridin-3-ylcarbamate (10a) To a solution of 2-bromopyridin-3-amine (3.0 g, 17.3 mmol) in tetrahydrofuran (THF, 30 mL) was slowly added lithium bis(trimethylsilyl)carbamate (1M, 35 mL, 35 mmol) at 0 °C. The reaction mixture was stirred at this temperature for 30 minutes. Subsequently, a solution of di-tert-butyl dicarbonate (Boc2O, 3.9 g, 17.3 mmol) in THF (20 mL) was added and the mixture was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the reaction mixture was poured into 0.1 M hydrochloric acid (HCl) and extracted with ethyl acetate (EA). The organic layers were combined, washed with saturated saline (brine), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (CC, petroleum ether/ethyl acetate = 5/1) to afford the target compound 10a (2.9 g, 62% yield) as a white solid.

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 16, p. 5032 - 5043
[2] Patent: WO2013/64231, 2013, A1. Location in patent: Page/Page column 51
[3] Patent: US2013/131036, 2013, A1. Location in patent: Paragraph 1676; 1677
[4] Patent: WO2013/62966, 2013, A2. Location in patent: Paragraph 203; 204
[5] Patent: WO2005/21529, 2005, A1. Location in patent: Page/Page column 31

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