Hexane → [2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-methanol

Temperature

5 °C

A 1.6 M solution of n-butyllithium in hexane (5.7 ml, 9.1 mmol) was added within 10 min to a −78° C. cold solution of N,N′-diisopropylethylamine (1.55 ml, 9.1 mmol) in THF (25.5 ml). The solution was stirred for 10 min at 5° C. and cooled again to −78° C. A solution of 2-(4-chloro-phenyl)-2H-indazole (1.7 g, 7.4 mmol; Liu, Rui; Zhu, Yong-ming; Qin, Lie-na; Ji, Shun-jun; Katayama, Haji. Heterocycles (2007), 71(8), 1755-1763.) in THF (8.5 ml) was added, the suspension was stirred for 15 min at 0° C., cooled to −78° C. and cyclohexane-carbaldehyde (1.1 ml, 9.1 mmol; CAS Reg. No. 2043-61-0) was added. The reaction mixture was stirred at ambient temperature for 14 h. Under ice cooling saturated aqueous ammonium chloride solution was added and the mixture was extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (1.1 g, 3.2 mmol; 43%) as yellow foam. MS: m/e=341.2 [M+H+].

1. temperaturecooled again to −78° C
2. stirringthe suspension was stirred for 15 min at 0° C.
3. temperaturecooled to −78° C.
4. addition2043-61-0) was added
5. stirringThe reaction mixture was stirred at ambient temperature for 14 h
6. additionUnder ice cooling saturated aqueous ammonium chloride solution was added
7. extractionthe mixture was extracted two times with iPrOAc
8. washThe combined extracts were washed with ice water/brine 1/1
9. dry with materialdried over Na2SO4
10. filtrationAfter filtration the solvent
11. customwas removed under reduced pressure
12. customthe residue was purified by column chromatography (silica gel, iPrOAc/heptane)

ORD record

ord-c33e5113487747a99d35aa60b656c5a0

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008505B2