Réaction #1973919

Équation de réaction

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

1-(ethoxymethyl)-1H-indole-4-carboxylic acid

cyclopropylamine

triethylamine

→

title compound

Rendement 77.0%

N-cyclopropyl-1-(ethoxymethyl)-1H-indole-4-carboxamide

Rendement 77.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe volatiles are removed in vacuo
2. 2
   workup.STIRRINGThe residue is stirred in EA (1.5 L)
3. 3
   workup.WAITHCl (0.5%, 1 L) for 10 minutes
4. 4
   AutreThe organic layer is separated
5. 5
   Lavagewashed with aqueous saturated sodium chloride (3×100 mL)
6. 6
   Séchagedried over anhydrous Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   AutreThe residue is purified by chromatography on silica gel

Mode opératoire

To a solution of 1-(ethoxymethyl)-1H-indole-4-carboxylic acid (123 g, 0.56 mol) in THF (1.5 L) is added cyclopropylamine (58 mL, 0.84 mol) and triethylamine (TEA, 167 mL, 1.12 mol), followed by O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (240 g, 0.62 mol) at 0° C. The reaction mixture is stirred at ambient temperature overnight. The volatiles are removed in vacuo. The residue is stirred in EA (1.5 L) and HCl (0.5%, 1 L) for 10 minutes. The organic layer is separated, washed with aqueous saturated sodium chloride (3×100 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue is purified by chromatography on silica gel to give the title compound (110 g, 77%). MS (m/z): 259 (M+H)+.

Source