Réaction #71436

Équation de réaction

3-nitropyrrole

cesium carbonate

1-chloro-2-dimethylaminoethane

→

title compound

Rendement 80.3%

Dimethyl-[2-(3-nitro-pyrrol-1-yl)-ethyl]-amine

Rendement 80.3%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was quenched by addition of a saturated aqueous solution of NaHCO3
2. 2
   Extractionextracted with DCM/MeOH (9:1
3. 3
   LavageThe organic phase was washed with a saturated aqueous solution of NaHCO3
4. 4
   Séchagedried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreThe residue was purified by silica gel column chromatography (DCM DCM/MeOH, 97:3)

Mode opératoire

A mixture of 3-nitropyrrole (500 mg, 4.46 mmol), cesium carbonate (3.63 g, 11.2 mmol, 2.5 equiv), 1-chloro-2-dimethylaminoethane (835 mg, 5.8 mmol, 1.3 equiv) and DMF (5 mL) was stirred for 16 h at rt. The reaction mixture was quenched by addition of a saturated aqueous solution of NaHCO3 and extracted with DCM/MeOH (9:1, v/v). The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM DCM/MeOH, 97:3) to afford 656 mg of the title compound as a yellow oil. Title compound: ESI-MS: 184.1 [M+H]+; TLC: Rf=0.38 (DCM/MeOH, 9:1).

Source