5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

238-240 °C (decomp)

Boiling point:

240°C(lit.)

Density 

1.838±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.68±0.30(Predicted)

form 

Solid

color 

White to Light yellow

InChI

InChI=1S/C9H6BrNO2/c10-5-1-2-8-6(3-5)7(4-11-8)9(12)13/h1-4,11H,(H,12,13)

InChIKey

JVZMBSGNSAHFCY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

10406-06-1(CAS DataBase Reference)

Safety Information

HS Code 

2933998090

5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID Usage And Synthesis

Uses

5-Bromo-1H-indole-3-carboxylic Acid is a useful intermediate used in the synthesis of indole derivatives that functions as inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase.

Synthesis

Lithium tert-butoxide (LiOtBu, 160 mg, 2.00 mmol) and 5-bromoindole (23.4 mg, 0.4 mmol) were added to a dry two-neck flask. The reaction vessel was evacuated and filled with carbon dioxide gas. Subsequently, N,N-dimethylformamide (DMF, 2 mL) was added and the mixture was stirred and reacted at 100 °C for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature, the reaction was carefully quenched with 2N hydrochloric acid solution and extracted with ethyl acetate (5 x 5 mL). The organic phases were combined, washed sequentially with water (2 x 5 mL) and saturated saline (1 x 5 mL) and dried over anhydrous magnesium sulfate. The dried organic phases were concentrated under reduced pressure and the residue was purified by preparative thin layer chromatography (Spreader: hexane/acetone=1:1, v/v) to afford the target compound 5-bromo-1H-indole-3-carboxylic acid (153.0 mg, 95% yield) as a white solid.

References

[1] Organic Letters, 2012, vol. 14, # 20, p. 5326 - 5329,4
[2] Heterocycles, 2015, vol. 90, # 2, p. 1196 - 1204

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