6-CHLORO-3-METHYL-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Boiling point:

288.7±35.0 °C(Predicted)

Density 

1.247±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-0.53±0.10(Predicted)

form 

wooly crystalline powder

color 

White

InChI

InChI=1S/C8H8ClNO2/c1-5-3-4-6(9)10-7(5)8(11)12-2/h3-4H,1-2H3

InChIKey

XWPSWOKQWBNRDW-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC(Cl)=CC=C1C

Safety Information

HS Code 

2933399990

6-CHLORO-3-METHYL-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Synthesis

2-(Methoxycarbonyl)-3-methylpyridin-1-en-1-ol salt (500 mg, 2.99 mmol, 1.00 eq.) was used as a starting material and dissolved in phosphoryl chloride (2 mL). The reaction mixture was stirred at 110 °C for 4 hours. Upon completion of the reaction, the reaction was quenched with ice water and the pH was adjusted to 7. Subsequently, the aqueous phase was extracted with ethyl acetate (3 × 10 mL). The organic layers were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:5, v/v) as eluent to afford methyl 6-chloro-3-methylpyridine-2-carboxylate (230 mg, 41% yield) as a white solid.LC-MS (ESI, m/z): 186 [M + H]+.

References

[1] Patent: US2015/57260, 2015, A1. Location in patent: Paragraph 1234; 1235
[2] Patent: WO2015/25026, 2015, A1. Location in patent: Page/Page column 268
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1736 - 1739
[4] Patent: WO2014/209727, 2014, A1. Location in patent: Page/Page column 69
[5] Patent: WO2014/205593, 2014, A1. Location in patent: Page/Page column 73

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