5-CYANO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

452.3±48.0 °C(Predicted)

Density 

1.58±0.1 g/cm3(Predicted)

storage temp. 

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

form 

Solid

color 

Pale yellow

Sensitive 

Light Sensitive

InChI

InChI=1S/C14H13IN2O2/c1-14(2,3)19-13(18)17-8-11(15)10-6-9(7-16)4-5-12(10)17/h4-6,8H,1-3H3

InChIKey

GADLXNFRAAUWAD-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)C2=C(C=C(C#N)C=C2)C(I)=C1

Safety Information

Hazard Codes 

Xi

HazardClass 

6.1

HS Code 

2933998090

5-CYANO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

The general procedure for the synthesis of tert-butyl 5-amino-3-iodo-1H-indole-1-carboxylate from 3-iodo-1H-indole-5-cyano and di-tert-butyl dicarbonate was as follows: 5-cyano-3-iodoindole (0.700 g, 2.61 mmol) was dissolved in dichloromethane (40 mL), and di-tert-butyl dicarbonate (0.627 g, 2.87 mmol) was added sequentially, triethylamine (1.09 mL, 7.83 mmol) and 4-dimethylaminopyridine (32.0 mg, 0.261 mmol). The reaction mixture was stirred at room temperature for 40 min. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed sequentially with 1 mol/L hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1-tert-butoxycarbonyl-5-cyano-3-iodoindole (0.958 g, quantitative yield). esi-ms: m/z 369 [M + H]+.

References

[1] Patent: EP2163554, 2010, A1. Location in patent: Page/Page column 107

5-CYANO-3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(864685-26-7)Related Product Information

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