ChemicalBook CAS DataBase List 5-Bromo-3-cyanoindole

5-Bromo-3-cyanoindole synthesis

8synthesis methods

Product Name:5-Bromo-3-cyanoindole
CAS Number:90271-86-6
Molecular formula:C9H5BrN2
Molecular Weight:221.05

10075-50-0

1189-71-5

90271-86-6

GENERAL METHOD: To a solution of 5-bromoindole (6.8 mmol) in anhydrous acetonitrile (6.0 mL) was slowly added chlorosulfonyl isocyanate (CSI) (0.63 mL, 7.25 mmol) dropwise at 0 °C, and the reaction mixture was kept stirring at 0 °C for 2 hours. Subsequently, anhydrous dimethylformamide (DMF) (1.3 mL, 170.0 mmol) was added dropwise and stirring was continued at 0 °C for 2 hours. Upon completion of the reaction, the mixture was poured into water and the resulting precipitate was collected by filtration. The precipitate was dried over anhydrous Na2SO4 and purified by column chromatography with the eluent being petroleum ether/ethyl acetate (40/60) or pure ethyl acetate to afford the target product 5-bromo-3-cyanoindole.

10075-50-0 Synthesis

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Yield: 91%

Reaction Conditions:

Stage #1:5-bromo-1H-indole;isocyanate de chlorosulfonyle in acetonitrile at 0; for 2 h;
Stage #2: with N,N-dimethyl-formamide in acetonitrile at 0; for 2 h;

Steps:

3.1.2. General Procedure for the Synthesis of 1H-Indole-3-carbonitriles (4a-d)
General procedure: To a solution of the appropriate indoles 3a-d (6.8 mmol) in anhydrous acetonitrile (6.0 mL),chlorosulfonyl isocyanate (CSI) (0.63 mL, 7.25 mmol) was added dropwise at 0 °C and the reactionmixture was stirred at 0 °C for 2 h. Anhydrous dimethylformamide (DMF) (1.3 mL, 170.0 mmol)was added dropwise and the mixture was stirred at 0 C for 2 h. The mixture was poured intoice-water and the obtained precipitate was filtered off, dried (anhydrous Na2SO4) and purified bycolumn chromatography using petroleum ether/ethyl acetate (40/60) (for 4b-d) or ethyl acetate (for4a) as eluent.

References:

Carbone, Anna;Parrino, Barbara;Cusimano, Maria Grazia;Spanò, Virginia;Montalbano, Alessandra;Barraja, Paola;Schillaci, Domenico;Cirrincione, Girolamo;Diana, Patrizia;Cascioferro, Stella [Marine Drugs,2018,vol. 16,# 8,art. no. 274]

877-03-2 Synthesis