3-(3-METHYL-1H-INDOL-1-YL)PROPANENITRILE synthesis

7synthesis methods

Product Name:3-(3-METHYL-1H-INDOL-1-YL)PROPANENITRILE
CAS Number:4414-81-7
Molecular formula:C12H12N2
Molecular Weight:184.24

83-34-1 Synthesis

83-34-1
500 suppliers
$12.00/10g

2417-90-5
119 suppliers
$18.00/1g

3-(3-METHYL-1H-INDOL-1-YL)PROPANENITRILE

4414-81-7
22 suppliers
inquiry

Yield:4414-81-7 74%

Reaction Conditions:

Stage #1: 3-Methylindolewith sodium hydride in N,N-dimethyl-formamide at 0; for 0.75 h;
Stage #2: bromopropionitrile in N,N-dimethyl-formamide at 20; for 6 h;

Steps:

General Procedure A: alkylation of 1 //-indole.

General procedure: In a 50 mL oven-dried round bottom flask, l/Z-indoles (1.71 mmol) was dissolved in 20 mL anhydrous DMF and cooled down to 0 °C. NaH (0.10 g, 2.57 mmol) was added portionwise. The resulting heterogeneous mixture was stirred at 0 °C for 45 min. 3-Bromopropanenitrile (0.21 mL, 2.57 mmol) was then added dropwise via syringe and the reaction mixture was allowed to warm up to room temperature. After 6 h, the reaction was quenched with 1M HC1, extracted two times with ethyl acetate and concentrated under vacuum. The crude product was purified via flash column chromatography to offer the desired product.

References:

WO2019/191410,2019,A1 Location in patent:Page/Page column 31; 35