Reaktion #1075291

Reaktionsgleichung

1-chloro-3-iodopropane

6-(3-thienyl)-1H-indazole

sodium hydride

→

2-(3-chloropropyl)-6-(3-thienyl)-2H-indazole

Ausbeute 28.0%

1-(3-chloropropyl)-6-(3-thienyl)-1H-indazole

Ausbeute 63.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir at room temperature overnight
2. 2
   Sonstigebefore quenching with brine (20 mL)
3. 3
   Sonstigepartitioning into ethyl acetate (100 mL)
4. 4
   Trocknendrying over anhydrous sodium sulfate
5. 5
   SonstigeThe solvent was removed in vacuo and flash chromatography (silica gel, 10-20% ethyl acetate in hexane)

Vorschrift

1-chloro-3-iodopropane (0.14 mL, 1.3 mmol) was added to a DMF (3 mL) solution of 6-(3-thienyl)-1H-indazole (88.4 mg, 0.44 mmol) and sodium hydride (60%, 72 mg, 1.8 mmol) that had been allowed to stir for 5 min at room temperature under argon. The reaction mixture was allowed to stir at room temperature overnight before quenching with brine (20 mL) and partitioning into ethyl acetate (100 mL), and drying over anhydrous sodium sulfate. The solvent was removed in vacuo and flash chromatography (silica gel, 10-20% ethyl acetate in hexane) yielded 1-(3-chloropropyl)-6-(3-thienyl)-1H-indazole (76.6 mg, 63%) as well as the side product 2-(3-chloropropyl)-6-(3-thienyl)-2H-indazole (33.9 mg, 28%).

Quelle