3-iodo-1H-indole-5-carbonitrile synthesis
- Product Name:3-iodo-1H-indole-5-carbonitrile
- CAS Number:1092114-59-4
- Molecular formula:C9H5IN2
- Molecular Weight:268.05
15861-24-2
1092114-59-4
Example 1 Synthesis of 3-iodo-1H-indole-5-carbonitrile (V) 1H-indole-5-carbonitrile (5 g, 35.2 mmol), potassium hydroxide (KOH, 7.90 g, 141 mmol) and iodine (I2, 8.90 g, 35.2 mmol) were suspended in 25 mL of N,N-dimethylformamide (DMF) under inert atmosphere. The reaction mixture was stirred at 10 °C for 30 min under light protection, followed by quenching the reaction with 0.1 M sodium thiosulfate (Na2S2O3) solution (150 mL). The resulting suspension was continued to be stirred for 30 min, then filtered, and the collected solid was washed with deionized water and dried under vacuum at 50 °C to constant weight. The final white solid product 3-iodo-1H-indole-5-carbonitrile (V) (9.0 g) was obtained in 95% yield. 1H-NMR (400 MHz, CDCl3) data: δ 8.78 (1H, broad peak); 7.80 (1H, single peak); 7.46-7.40 (3H, multiple peaks).
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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