3-iodo-1H-indole-5-carbonitrile synthesis

Yield: 95%

Reaction Conditions:

with iodine;potassium hydroxide in N,N-dimethyl-formamide at 10; for 0.5 h;Inert atmosphere;Darkness;

Steps:

1 Synthesis of 3-iodo-1H-indole-5-carbonitrile (V)
Example 1
Synthesis of 3-iodo-1H-indole-5-carbonitrile (V)
1H-indole-5-carbonitrile (5 g, 35.2 mmol), KOH (7.90 g, 141 mmol) and I₂ (8.90 g, 35.2 mmol) are suspended in 25 mL of DMF under inert atmosphere.
The reaction is maintained under stiffing in the dark for 30 min at 10° C., and then treated with an 0.1M solution of Na₂S₂O₃ (150 mL) The resulting suspension is maintained under stirring for 30 min, then filtered, and the resulting solid is washed with water and dried at 50° C. under vacuum to constant weight.
Product (V) (9.0 g) is obtained as a white solid with a yield of 95%.
¹H-NMR (400 MHz, CDCl₃), δ: 8.78 (1H, bs); 7.80 (1H, s); 7.46-7.40 (3H, m).

References:

DIPHARMA FRANCIS S.R.L.;TADDEI, Maurizio;GIANNOTTI, Luca;ATTOLINO, Emanuele;ALLEGRINI, Pietro US2014/275542, 2014, A1 Location in patent:Paragraph 0060; 0061