Réaction #78400

Équation de réaction

solution

1-methyl-N-(3,4,5-trimethoxyphenyl)-1H-indole-5-sulfonamide

dimethylaminoacetyl chloride hydrochloride

diisopropylethylamine

→

desired product

Rendement 92.0%

N-((dimethylamino)acetyl)-1-methyl-N-(3,4,5-trimethoxyphenyl)-1H-indole-5-sulfonamide

Rendement 92.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated
2. 2
   workup.ADDITIONThe mixture was diluted with ethyl acetate (400 mL)
3. 3
   Lavagewashed with 5% NaHCO3 (2×200 mL) and water (200 mL)
4. 4
   Séchagedried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated to a volume of 120 mL
7. 7
   workup.ADDITIONdiluted with methyl tert-butyl ether (120 mL)
8. 8
   workup.STIRRINGstirred for 18 hours
9. 9
   workup.STIRRINGstirred for 2 hours
10. 10
    Filtrationfiltered
11. 11
    LavageThe resulting solid was washed with 1:1 ethyl acetate/methyl tert-butyl ether (100 mL)
12. 12
    Autredried under vacuum

Mode opératoire

A solution of Example 4 (20.0 g, 53.2 mmol) in THF (250 mL) at room temperature was treated with dimethylaminoacetyl chloride hydrochloride (12.3 g, 77.8 mmol), DMAP (650 mg, 5.3 mmol), and diisopropylethylamine (25.2 g, 195.0 mmol), stirred for 8 hours, and concentrated to ⅓ its original volume. The mixture was diluted with ethyl acetate (400 mL), washed with 5% NaHCO3 (2×200 mL) and water (200 mL), dried (Na2SO4), filtered, concentrated to a volume of 120 mL, diluted with methyl tert-butyl ether (120 mL), stirred for 18 hours, cooled to 0° C., stirred for 2 hours, and filtered. The resulting solid was washed with 1:1 ethyl acetate/methyl tert-butyl ether (100 mL) and dried under vacuum to provide 22.5 g (92%) of the desired product.

Source