1,2-Dimethoxyethane → 7-(2,4-dichloro-phenyl)-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazole

Temperatur

85 °C

A mixture of 7-bromo-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazole (1.47 g, 4.79 mmol), 2,4-dichlorophenyl boronic acid (1.32 g, 6.94 mmol), 18 mL of ethylene glycol dimethyl ether, tetrakis(triphenylphosphine)palladium(0) (0.166 g, 0.143 mmol), and 20 mL of a 2 M aqueous Na2CO3 solution was stirred at 85° C. overnight, then allowed to cool. Ethyl acetate (50 mL) was added, and the mixture was washed with two 40 mL portions of a saturated aqueous NaCl solution. The combined aqueous layers were extracted with 20 mL of ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated to a brown oil. Column chromatography (0→5% EtOAc/hexanes) afforded 7-(2,4-dichloro-phenyl)-2-methyl-3-((E)-1-propyl-but-1-enyl)-2H-indazole (15a; 1.57 g; 88%) as a white solid.

1. temperatureto cool
2. washthe mixture was washed with two 40 mL portions of a saturated aqueous NaCl solution
3. extractionThe combined aqueous layers were extracted with 20 mL of ethyl acetate
4. dry with materialThe combined organic layers were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated to a brown oil

ORD-Eintrag

ord-603f9f3c47f2492ba555c6aee0832ff6

Quelldatensatz

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07365211B2