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

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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