5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester Chemical Properties

Boiling point:

311℃

Density 

1.684

Flash point:

142℃

storage temp. 

Inert atmosphere,Room Temperature

pka

-3.26±0.10(Predicted)

form 

crystalline powder

color 

White

InChI

InChI=1S/C7H5BrClNO2/c1-12-7(11)6-5(9)2-4(8)3-10-6/h2-3H,1H3

InChIKey

QBNSPYFGGCZDJG-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=C(Br)C=C1Cl

Safety Information

HS Code 

2933399990

5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester Usage And Synthesis

Uses

5-Bromo-3-chloro-2-pyridinecarboxylic Acid Methyl Ester is an intermediate used to prepare aminopyridinyldihydrooxazine derivatives for use as BACE-1 and/or BACE-2 inhibitors.

Synthesis

To a solution of dichloromethane (700 mL) containing traces of turbid 5-bromo-3-chloropyridine-2-carboxylic acid (60 g, 183.2 mmol), N,N-dimethylformamide (1 mL) and oxalyl chloride (24.9 mL, 286.9 mmol) were added slowly and dropwise. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the resulting yellow solution was cooled to 10 °C and methanol (30.8 mL, 761.3 mmol) was slowly added dropwise at this temperature, keeping the reaction temperature between 15 °C and 20 °C. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature overnight. At the end of the reaction, the reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution, followed by washing the organic layer with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give methyl 5-bromo-3-chloro-2-pyridinecarboxylate (55 g) as a yellow solid, which could be used in the next reaction without further purification.LCMS (Method B): m/z 250/252/254 (M + 1), retention time 1.12 min.

References

[1] Patent: WO2015/160636, 2015, A1. Location in patent: Page/Page column 164
[2] Patent: WO2015/160634, 2015, A1. Location in patent: Page/Page column 145
[3] Patent: WO2016/46071, 2016, A1. Location in patent: Page/Page column 61
[4] Patent: WO2016/87265, 2016, A1. Location in patent: Page/Page column 62; 63
[5] Patent: WO2016/87257, 2016, A1. Location in patent: Page/Page column 67-68

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