Reaktion #822594

Reaktionsgleichung

Sodium hydride

3-(2,4-dimethoxyphenyl)-7-(trifluoromethyl)-1H-indazole

allyl bromide

→

title compound

Ausbeute 34.9%

2-ALLYL-3-(2,4-DIMETHOXYPHENYL)-7-(TRIFLUOROMETHYL)-2H-INDAZOLE

Ausbeute 34.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cool reaction mixture
2. 2
   Sonstigewas partitioned with EtOAc and 1 N HCl
3. 3
   WaschenThe organic phase was washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   SonstigeThe resulting residue was purified by flash chromatography or by HPLC chromatography through silica gel columns, 150×12 mm (Biotage, Charlottesville, Va.), at 10 mL/min with methyl-t-butyl ether/hexane (gradient elution, 1:9 to 1:1)

Vorschrift

Sodium hydride (60% in oil, 0.025 g, 1.04 mmol) was added in one portion to a solution of 3-(2,4-dimethoxyphenyl)-7-(trifluoromethyl)-1H-indazole (0.150 g, 0.49 mmol) in DMF. After the gas evolution ceased, allyl bromide (0.07 mL, 0.7 mmol) was added and the reaction mixture was stirred at ambient temperature to 50° C. overnight. The cool reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). The resulting residue was purified by flash chromatography or by HPLC chromatography through silica gel columns, 150×12 mm (Biotage, Charlottesville, Va.), at 10 mL/min with methyl-t-butyl ether/hexane (gradient elution, 1:9 to 1:1) to give the title compound (0.062 g) as a white solid.

Quelle