Reaktion #332974

Reaktionsgleichung

6-chloro-3-iodo-1H-indazole

Potassium tert-butoxide

Methyl iodide

→

6-chloro-3-iodo-1-methyl-1H-indazole

Ausbeute 66.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe ice bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 2 h
3. 3
   SonstigeThe reaction mixture was quenched with water
4. 4
   Extraktionextracted with EtOAc (2×)
5. 5
   WaschenThe combined organic layers were washed with water and brine
6. 6
   Trocknenthen dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was purified by chromatography over silica gel with EtOAc/Hexanes (gradient 0-5% EtOAc)

Vorschrift

In a round-bottomed flask, 6-chloro-3-iodo-1H-indazole (167 mg, 0.57 mmol) was dissolved in THF (2 ml) and the solution was cooled to 0° C. Potassium tert-butoxide (90 mg, 0.80 mmol) was added and the reaction mixture was stirred at 0° C. for 1.25 h. Methyl iodide (0.045 ml, 0.72 mmol) was added dropwise then the ice bath was removed and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography over silica gel with EtOAc/Hexanes (gradient 0-5% EtOAc) to afford 110 mg (63%) of 6-chloro-3-iodo-1-methyl-1H-indazole as a yellow solid.

Quelle