1-Boc-4-chloro-3-formylindole Chemical Properties

Boiling point:

409.4±48.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

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

Appearance

White to off-white Solid

Safety Information

HS Code 

2933998090

1-Boc-4-chloro-3-formylindole Usage And Synthesis

Synthesis

General procedure for the synthesis of 1-Boc-4-chloro-3-formylindole from 4-chloroindole-3-carboxaldehyde and di-tert-butyl dicarbonate: To a solution of 4-chloroindole-3-carboxaldehyde (1.0 eq.) and di-tert-butyl dicarbonate (1.2 eq.) in acetonitrile was added DMAP (0.1 eq.). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution. The organic and aqueous phases were separated. The aqueous phase was extracted with dichloromethane. All organic phases were combined and washed sequentially with saturated ammonium chloride solution, water and brine. The organic phase was dried with magnesium sulfate, filtered and concentrated under reduced pressure. The resulting BOC-protected 1-Boc-4-chloro-3-formylindole can be used in the next step without further purification.

References

[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9179 - 9195
[2] Patent: WO2013/45516, 2013, A1. Location in patent: Page/Page column 129; 151

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