Methane → HCID 67164517, Verbindung

HRID 12205

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:21]([O-])=O)[C:14]=1[S:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[Cl-].[NH4+].C>C(O)C.C(OCC)(=O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:21])[C:14]=1[S:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A 50 ml round-bottom flask with a magnetic stirrer was charged with [2-(6-chloro-8-nitro-9H-β-carbolin-7-ylsulfanyl)-ethyl]-dimethyl-amine (106 mg, 0.30 mmol) in 8 ml of anhydrous ethanol. To the resulting orange mixture at RT was added 0.33 M aqueous ammonium chloride (1.95 ml, 0.64 mmol) and iron powder (540 mg, 9.67 mmol). The reaction mixture was heated to 60° C. and stirred vigorously for 20 hr. Next, the mixture was cooled to RT, diluted with ethyl acetate (20 ml) and activated charcoal (ca. 150 mg) was added. The resulting mixture was filtered through a pad of celite and the resulting filtrate concentrated to afford 103 mg of 6-chloro-7-(2-dimethylamino-ethylsulfanyl)-9H-β-carbolin-8-ylamine as a yellow solid. The crude product was used directly in the coupling step.

Aufarbeitung

temperatureNext, the mixture was cooled to RT
additionwas added
filtrationThe resulting mixture was filtered through a pad of celite
concentrationthe resulting filtrate concentrated

Quellen und Nachweise

ORD-Eintrag: ord-6cee690533f34e0b838930aeaf183eee
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07727985B2

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