TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE Chemical Properties

Melting point:

56-57 °C(lit.)

Boiling point:

367.9±34.0 °C(Predicted)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

color 

White to off-white

InChI

InChI=1S/C13H14BrNO2/c1-13(2,3)17-12(16)15-7-6-9-8-10(14)4-5-11(9)15/h4-8H,1-3H3

InChIKey

PBWDRTGTQIXVBR-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)C2=C(C=C(Br)C=C2)C=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE Usage And Synthesis

Uses

N-Boc-5-bromoindole is formed as an intermediate for the synthesis of di-Boc-protected 5-aminoindole via a Buchwald-Hartwig amination with tBu-carbamate followed by regioselective bromination[1].

General Description

N-Boc-5-bromoindole can undergo Sonogashira coupling reaction with N,N-diisopropylprop-2-ynylamine to afford the corresponding propargylic diisopropylamine. N-Boc-5-bromoindole is formed as an intermediate during the synthesis of 2-(5-substituted-1H-indol-3-yl)-N-hydroxyacetamide derivatives.

Synthesis

5-Bromoindole (5.0 g, 25.5 mmol), di-tert-butyl dicarbonate (7.6 mL, 33.1 mmol) and 4-dimethylaminopyridine (0.15 g, 1.23 mmol) were dissolved in acetonitrile (50 mL) and the reaction was stirred for 3 h at room temperature. After completion of the reaction, aqueous citric acid was added to the reaction mixture and extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-tert-butoxycarbonyl-5-bromoindole (7.8 g, 100% yield) as a light yellow oil.

References

[1] Christoffer Bengtsson, et al. Rapid Construction of a Chloromethyl-Substituted Duocarmycin-like Prodrug. Molecules. 2023 Jun 16;28(12):4818. DOI:10.3390/molecules28124818

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