Sodium hydride → N-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-2,N-dicyclohexyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To an ice cold suspension of NaH (13 mg, 340 μmol) in DMF (5 ml) under an argon atmosphere was added a solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-amine (100 mg, 310 μmol; example 11.1) in DMF (1 ml) within 10 min. The suspension was stirred for 1 h at 0° C. A solution of cyclohexyl-acetyl chloride (50 μl, 340 μmol; [23860-35-7]) in DMF (1 ml) was added within 5 min. The reaction mixture was stirred for 14 h at ambient temperature, poured onto ice water/brine 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (8 mg, 20 μmol; 6%) as yellow oil. MS: m/e=450.0 [M+H+].

Provenance & Evidence