1-(3-METHYLBENZYL)-1H-INDOLE-3-CARBALDEHYDE synthesis
- Product Name:1-(3-METHYLBENZYL)-1H-INDOLE-3-CARBALDEHYDE
- CAS Number:428470-09-1
- Molecular formula:C17H15NO
- Molecular Weight:249.31
487-89-8
616 suppliers
$6.00/10g
620-13-3
165 suppliers
$10.00/1g
428470-09-1
11 suppliers
$95.00/500mg
Yield:428470-09-1 86%
Reaction Conditions:
Stage #1: Indole-3-carboxaldehydewith sodium hydride in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 0.5 h;Inert atmosphere;
Stage #2: 1-bromomethyl-3-methyl-benzene in N,N-dimethyl-formamide;mineral oil at 20;Inert atmosphere;
Steps:
4.1.3 General procedure B for the synthesis of N-alkyl-indole-3-carboxaldehyde (39a-39p)
General procedure: To a suspension of NaH 60% in oil (2.25equiv.) in dry DMF (0.8mL/mmol) was added, at 0°C and under nitrogen atmosphere, a solution of indolecarboxaldehyde (1equiv.) in dry DMF (2.5mL/mmol). After stirring for 30min at rt, alkyl halide (1.0-3.0equiv.) was slowly added. After stirring overnight, the reaction was quenched by addition of water and the product was extracted with diethyl ether. The organic layer was dried over MgSO4, filtered off and concentrated under vacuum. The crude product was purified by column chromatography on silica gel.
References:
Meguellati, Amel;Ahmed-Belkacem, Abdelhakim;Yi, Wei;Haudecoeur, Romain;Crouillère, Marie;Brillet, Rozenn;Pawlotsky, Jean-Michel;Boumendjel, Ahcène;Peuchmaur, Marine [European Journal of Medicinal Chemistry,2014,vol. 80,p. 579 - 592]
487-89-8
616 suppliers
$6.00/10g
428470-09-1
11 suppliers
$95.00/500mg