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

Melting point:

143-148°C

Boiling point:

286.5±25.0 °C(Predicted)

Density 

1.453±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.26±0.70(Predicted)

form 

solid

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

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

Synthesis

5-Bromonicotinic acid (10 g, 49.5 mmol) was dissolved in tert-butanol (100 mL) at 20 °C and triethylamine (15.2 g, 150 mmol) and DPPA (20.4 g, 74 mmol) were added. The mixture was stirred in toluene (100 mL) at 65 °C for 40 min, followed by heating to 100 °C under nitrogen protection for 22 h of reaction. After completion of the reaction, the mixture was cooled and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane as eluent to afford tert-butyl 5-bromopyridine-3-carboxylate (10.52 g, 78%) as a white solid.1H NMR (300 MHz, CDCl3) δ 8.32 (m, 3H), 6.97 (brs, 1H), 1.53 (s, 9H); MS (ES) m/z: 273, 275 (M+H+). Calculated analytical value C10H13N2O2Br: C, 43.98; H, 4.80; N, 10.26. Measured value: C, 43.88; H, 4.52; N, 10.20.

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 695 - 709
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4535 - 4546
[3] Patent: WO2004/9562, 2004, A1. Location in patent: Page 31-33
[4] Patent: WO2006/82373, 2006, A1. Location in patent: Page/Page column 107
[5] Patent: US2008/194552, 2008, A1. Location in patent: Page/Page column 31

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