(4-CHLORO-PYRIDIN-2-YL)-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

(dec)

Boiling point:

274℃

Density 

1.245

Flash point:

120℃

storage temp. 

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

pka

11.89±0.70(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C10H13ClN2O2/c1-10(2,3)15-9(14)13-8-6-7(11)4-5-12-8/h4-6H,1-3H3,(H,12,13,14)

InChIKey

ATOQLEMIFREXLS-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1=NC=CC(Cl)=C1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-43

Safety Statements 

36/37

HazardClass 

IRRITANT

HS Code 

2933399990

(4-CHLORO-PYRIDIN-2-YL)-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

tert-Butyl (4-chloropyridin-2-yl)carbamate is used as an organic synthesis intermediate and a pharmaceutical intermediate for laboratory research and development processes and in the synthesis of pharmaceutical chemicals.

Synthesis

LHMDS (1 M tetrahydrofuran solution, 17.11 mL, 17.11 mmol) was dissolved in tetrahydrofuran (5 mL) at -5 °C and tetrahydrofuran solution (5 mL) of 4-chloropyridin-2-amine (1 g, 7.78 mmol) was slowly added and stirred for 5 min. Subsequently, tetrahydrofuran solution (5 mL) of di-tert-butyl dicarbonate (Boc2O, 1.898 mL, 8.18 mmol) was added to the reaction mixture. The reaction system was maintained at 0°C and stirring was continued for 2 h. Upon completion of the reaction, the reaction was quenched by the addition of aqueous ammonium chloride solution. The pH of the reaction solution was adjusted to 6 with 1.5 N hydrochloric acid, followed by extraction with ethyl acetate (3 x 15 mL). The organic phases were combined and washed sequentially with sodium bicarbonate solution (15 mL), water (15 mL) and brine (15 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient elution with ethyl acetate/petroleum ether) to afford the target product tert-butyl (4-chloropyridin-2-yl)carbamate (1.435 g, 6.28 mmol, 81% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 10.10 (s, 1H), 8.23 (d, J = 5.20 Hz, 1H), 7.88 (d, J = 2.00 Hz, 1H), 7.15 (dd, J = 2.00, 5.20 Hz, 1H), 1.48 (s, 9H).

References

[1] Angewandte Chemie - International Edition, 2015, vol. 54, # 20, p. 6037 - 6040
[2] Angew. Chem., 2015, vol. 127, # 20, p. 6135 - 6138,4
[3] Patent: WO2015/116060, 2015, A1. Location in patent: Page/Page column 97
[4] Patent: JP2015/528018, 2015, A. Location in patent: Paragraph 0198
[5] Patent: WO2011/139891, 2011, A1. Location in patent: Page/Page column 54

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