Sodium Bicarbonate → Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

HRID 1080804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1080804
[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[CH:13]3)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33].[Al].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[C:13]3[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 5359268AluminumHCID 544874815-(Cyclopentyloxycarbonyl)amino-1-methylindole

Produkt 1

HCID 11453373Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 5-(cyclopentyloxycarbonyl)amino-1-methylindole (AA) (1.3 g.) and methyl 4-bromomethyl-3-methoxybenzoate (B) (1.3 g.) in N,N-dimethylformamide (25 ml.) was stirred and heated at 100° C., under a nitrogen atmosphere, while protecting the reaction vessel from light with aluminum foil, for 24 hours. The cooled mixture was poured onto saturated aqueous sodium bicarbonate solution (300 ml.), extracted with ethyl acetate (3×100 ml.), the combined extracts washed with brine (50 ml.), dried (MgSO4), and evaporated. The product was isolated by flash chromatography on silica gel (3.5 cm. diameter column) to give the title compound (P) (0.98 g., 45%), identical with that obtained in Example 8.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×100 ml.)
  2. washthe combined extracts washed with brine (50 ml.)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe product was isolated by flash chromatography on silica gel (3.5 cm. diameter column)

Quellen und Nachweise

ORD-Eintrag
ord-92132dd4a7374ea0af414dcad6bea3c8
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05583152

Notizen zur Reaktion

Wird geladen…