5-Bromo-2,3-dimethylindole Chemical Properties

Melting point:

136-137℃

Boiling point:

135-137 °C(Press: 10 Torr)

Density 

1.487

refractive index 

1.5923

storage temp. 

2-8°C

pka

16.91±0.30(Predicted)

Appearance

Light yellow to orange Solid

Safety Information

HS Code 

2933998090

5-Bromo-2,3-dimethylindole Usage And Synthesis

Uses

5-Bromo-2,3-dimethylindole is used to prepare 1-[(arylsulfonyl)amino]alkylindole derivatives as dual thromboxane synthase inhibitor/thromboxane receptor antagonists. It is also used to prepare modulators of secreted frizzled related protein-1 (SFRP-1).

Synthesis

Procedure for the synthesis of 5-bromo-2,3-dimethylindole: A mixture of 4-bromophenylhydrazine (5.0 g, 22.3 mmol) and 2-butanone (1.6 g, 22.3 mmol) was dissolved in ethanol (60 mL) and the reaction was heated overnight under reflux conditions. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized from the ethanol/water solvent mixture to afford the target product 5-bromo-2,3-dimethylindole (3.6 g, 73% yield). The structure of the product was confirmed by NMR hydrogen spectrum (400 MHz, d6-DMSO): δ 10.87 (s, 1H), 7.51 (d, J = 1.2 Hz, 1H), 7.18 (d, J = 6.3 Hz, 1H), 7.07 (dd, J = 6.3 Hz, 1.2 Hz, 1H), 2.31 (s, 3H), 2.13 (s, 3H).

References

[1] Patent: WO2015/74123, 2015, A1. Location in patent: Page/Page column 47

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