METHYL 6-AMINO-5-BROMOPICOLINATE Chemical Properties

Melting point:

143-145 °C

Boiling point:

359.2±37.0 °C(Predicted)

Density 

1.662

storage temp. 

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

pka

-0.23±0.10(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C7H7BrN2O2/c1-12-7(11)5-3-2-4(8)6(9)10-5/h2-3H,1H3,(H2,9,10)

InChIKey

OQUCMNQHZFOMPC-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

METHYL 6-AMINO-5-BROMOPICOLINATE Usage And Synthesis

Uses

Methyl 6-amino-5-bromopicolinate is used in the preparation of aminopyridinamides as sodium channel modulators.

Synthesis

d) Synthesis of methyl 6-amino-5-bromopyridine-2-carboxylate: Methyl 6-aminopyridine-2-carboxylate (10 g, 66.0 mmol) was dissolved in chloroform (450 mL) at room temperature, and a chloroform (100 mL) solution of bromine (3.4 mL, 66.0 mmol) was slowly added. The reaction mixture was stirred for 40 hours, then diluted with chloroform and washed sequentially with saturated sodium thiosulfate solution and water. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using ethyl acetate/hexane as eluent to afford methyl 5-bromo-6-aminopyridine-2-carboxylate as a yellow solid (3.3 g, 22% yield).MS ESI (m/e): 231.0 [(M + H)+].1H NMR (CDCl3, 400 MHz): δ ( ppm) = 7.76 (d, J = 7.88 Hz, 1H), 7.34 (d, J = 7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H). (d) Isolation of methyl 6-amino-3-bromopyridine-2-carboxylate: In step d), the isomer methyl 6-amino-3-bromopyridine-2-carboxylate was isolated as a by-product to give methyl 6-amino-3-bromopyridine-2-carboxylate (3.0 g, 19% yield).MS ESI (m/e): 231.2 [(M + H)+].1H NMR (CDCl3, 400 MHz): δ (ppm) = 7.60 (d , J = 8.72 Hz, 1H), 6.47 (d, J = 7.88 Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).

References

[1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Organic Process Research and Development, 2010, vol. 14, # 1, p. 263 - 271
[3] Tetrahedron Letters, 2010, vol. 51, # 38, p. 5035 - 5037
[4] Patent: US2011/190269, 2011, A1. Location in patent: Page/Page column 61-62
[5] Patent: WO2011/92272, 2011, A1. Location in patent: Page/Page column 129; 130

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