METHYL 3-BROMOINDOLE-6-CARBOXYLATE Chemical Properties

Boiling point:

386.2±22.0 °C(Predicted)

Density 

1.629

storage temp. 

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

pka

14.13±0.30(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C10H8BrNO2/c1-14-10(13)6-2-3-7-8(11)5-12-9(7)4-6/h2-5,12H,1H3

InChIKey

YSCNGZSJIYDSOC-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(C(OC)=O)=C2)C(Br)=C1

METHYL 3-BROMOINDOLE-6-CARBOXYLATE Usage And Synthesis

Uses

Methyl 3-bromoindole-6-carboxylate is an organic synthesis intermediate, mainly used in the synthesis of indole-containing compounds, such as drugs, dyes and other chemical products.

Synthesis

Methyl 1H-indole-6-carboxylate (1.00 g, 5.71 mmol) was dissolved in anhydrous DMF (10 mL) under nitrogen atmosphere. A solution of N-bromosuccinimide (NBS, 1.04 g, 5.84 mmol) in anhydrous DMF (10 mL) was added slowly dropwise at -60 °C over 20 min. The reaction mixture was stirred at -60 °C, followed by a slow warming to room temperature over 3 hours. Upon completion of the reaction, it was extracted with ethyl acetate (100 mL) and water (20 mL, repeated three times). The organic layers were combined and the solvent was removed by vacuum concentration. The residue was purified by silica gel column chromatography with the eluents being petroleum ether and ethyl acetate (the proportion of ethyl acetate was increased in a gradient from 0%) to give methyl 3-bromoindole-6-carboxylate (1.41 g, 98% yield). The product was characterized by 1H NMR (600 MHz, CD3OD): δ 8.15 (s, 1H), 7.80 (d, J = 6.0 Hz, 1H), 7.50 (m, 2H), 3.94 (s, 3H).

References

[1] Patent: WO2017/197240, 2017, A1. Location in patent: Page/Page column 204
[2] Patent: WO2009/147121, 2009, A1. Location in patent: Page/Page column 35
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 4, p. 626 - 630
[4] Patent: US2005/165049, 2005, A1. Location in patent: Page/Page column 15
[5] Patent: WO2017/184658, 2017, A1. Location in patent: Page/Page column 19; 20

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