4-Heptanone → 4-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol

Temperatur

2.5 °C

To a solution of 7-bromo-2-methyl-2H-indazole (1.5 g, 7.1 mmol) in 18 mL of THF at −78° C. was added a 2 M solution of lithium diisopropylamide in heptane/ethylbenzene/THF (5.3 mL, 11 mmol). The solution was stirred at 0-5° C. for 10 m, then rechilled to −78° C. To it was added 4-heptanone (1.49 mL, 10.6 mmol), and the solution was stirred overnight, allowing to slowly warm to room temperature. A saturated aqueous NaHCO3 solution (40 mL) was added, and the mixture was extracted with three 30 mL portions of ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated to a brown solid. Column chromatography (0→20% EtOAc/hexanes) afforded 4-(7-bromo-2-methyl-2H-indazol-3-yl)-heptan-4-ol (42; 1.80 g; 78%).

1. customrechilled to −78° C
2. stirringthe solution was stirred overnight
3. temperatureto slowly warm to room temperature
4. extractionthe mixture was extracted with three 30 mL portions of ethyl acetate
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated to a brown solid

ORD-Eintrag

ord-ef09b8f2e6f547d09b8fcedd28f5bf1f

Quelldatensatz

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07365211B2