TERT-BUTYL 5-NITRO-1H-INDOLE-1-CARBOXYLATE Chemical Properties

Melting point:

115℃

storage temp. 

2-8°C

form 

solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

TERT-BUTYL 5-NITRO-1H-INDOLE-1-CARBOXYLATE Usage And Synthesis

Synthesis

Di-tert-butyl dicarbonate (524 mg, 2.4 mmol) and 5-nitro-1H-indole (325 mg, 2.0 mmol) were used as raw materials and stirred in dichloromethane (6 mL) for 5 min at 0 °C. Subsequently, a catalytic amount of 4-dimethylaminopyridine (3 mg, 0.025 mmol) was added and stirring was continued for 30 min at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (2 mL) and extracted with dichloromethane (15 mL x 3). The organic phases were combined, washed sequentially with water (20 mL) and saturated brine (15 mL × 2) and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to afford the gray solid product tert-butyl 5-nitro-1H-indole-1-carboxylate (526 mg, 100% yield), which could be used in the next reaction without further purification.

References

[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 15, p. 6273 - 6277
[2] Patent: CN104311541, 2017, B. Location in patent: Paragraph 0162; 0163
[3] Synthesis, 2009, # 21, p. 3617 - 3632
[4] Patent: WO2016/176460, 2016, A1. Location in patent: Page/Page column 96
[5] Patent: US2009/247568, 2009, A1. Location in patent: Page/Page column 35-36

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