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

Melting point:

79.4-79.6°C

Boiling point:

295.0±25.0 °C(Predicted)

Density 

1.212±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

12.42±0.70(Predicted)

color 

Light Yellow

InChI

InChI=1S/C11H14N2O3/c1-11(2,3)16-10(15)13-8-5-4-6-12-9(8)7-14/h4-7H,1-3H3,(H,13,15)

InChIKey

AHTZIHDCJWVLKK-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1=CC=CN=C1C=O

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36-43-36/37/38

Safety Statements 

26-36/37-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

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

Chemical Properties

White to off-white solid

Synthesis

Step 2: Synthesis of tert-butyl (2-formylpyridin-3-yl)carbamate (10b) To a solution of compound 10a (2.9 g, 10.7 mmol) in tetrahydrofuran (THF, 30 mL) was slowly added n-butyllithium (n-BuLi, 2.5 M, 8.5 mL, 21.4 mmol) at -78 °C and protected by nitrogen (N2). The reaction mixture was stirred continuously at this temperature for 1 hour. Subsequently, N-formylpiperidine (1.3 mL, 11.8 mmol) was added under fast stirring conditions. The reaction system was warmed up to 0 °C and stirring was continued for 1 hour. Upon completion of the reaction, it was partitioned with 1.5 M hydrochloric acid (HCl) solution. The pH of the aqueous layer was adjusted to 7 by addition of solid sodium carbonate (Na2CO3).The aqueous layer was extracted twice with ethyl acetate (EA), the organic layers were combined and dried with anhydrous sodium sulfate (Na2SO4). After concentration under reduced pressure, purification by column chromatography (CC, petroleum ether/ethyl acetate = 3/1) afforded the target compound 10b (1.5 g, 65% yield) as a white solid.

References

[1] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2136 - 2145
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 16, p. 5032 - 5043
[3] Patent: WO2013/64231, 2013, A1. Location in patent: Page/Page column 51

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