1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 178505448, Verbindung

HRID 250024

Reaktionsgleichung

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([NH2:11])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:12](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:13]>ClCCl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]=[C:12]=[S:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To 6-fluoro-1H-indazol-3-amine (0.32 g, 2.1 mmol) in dichloromethane (15 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.53 g, 2.30 mmol). The reaction was stirred at 50° C. for 3 hours. The reaction was cooled to room temperature and the crude product was purified by column chromatography (25% ethyl acetate/hexanes) to afford 6-fluoro-3-isothiocyanato-1H-indazole (0.30 g, 1.53 mmol, 73.0% yield) as a light yellow powder. 1H NMR (500 MHz, DMSO-D6) δ ppm 13.39 (s, 1 H), 7.78 (dd, J=8.85, 4.88 Hz, 1 H), 7.41 (dd, J=9.31, 1.68 Hz, 1 H), 7.14 (td, J=9.16, 1.83 Hz, 1 H). MS (LC/MS) R.T.=3.69; [M+H]+=194.07.

Aufarbeitung

temperatureThe reaction was cooled to room temperature
customthe crude product was purified by column chromatography (25% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-e0ee9f76af004c94842fb35a16627a91
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07863291B2

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