4-Nitro-1H-indole → HCID 59743448, Verbindung

Reaktionsgleichung

CC(C)=O.C(=O)=O.[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2)([O-:10])=[O:9].Cl[C:21]1([S:27][CH3:28])C=CN=[CH:23][NH:22]1.[C:29](#[N:31])[CH3:30].C1COCC1>>[CH3:28][S:27][C:21]1[N:22]=[C:23]([N:15]2[C:16]3[C:12](=[C:11]([N+:8]([O-:10])=[O:9])[CH:19]=[CH:18][CH:17]=3)[CH:13]=[CH:14]2)[CH:30]=[CH:29][N:31]=1

Komponenten

Edukt 4

HCID 1457664-Nitro-1H-indole

HCID 18522661Acetone cardice

HCID 22177404Acetonitrile tetrahydrofuran

HCID 178503302HCID 178503302, Verbindung

Produkt 1

HCID 59743448HCID 59743448, Verbindung

Versuchsvorschrift

A solution of sodium(bistrimethylsilyl)amide (1 M in THF, 26.42 mL) was slowly added to a cooled (acetone/dry-ice bath) solution of 4-nitroindole (4.2 g, 25.9 mmol) in a mixture of acetonitrile/THF (2/1, 75 mL) and the resulting mixture was stirred for 1 hour. 4-Chloro-4-methylthiopyrimidine (4.202 g, 26.2 mmol) was then added and the reaction mixture was warmed to RT and stirred for 21 h. The resulting mixture was evaporated under reduced pressure and the solid residue was triturated with a mixture of hexane/EtOAc/Et2O (5/1/1). The solid was collected by filtration, washed and dried under reduced pressure to give 2.56 g of 1-(2-methylsulfanyl-pyrimidin-4-yl)-4-nitro-1H-indole which was used without further purification.