Pyridine → 4-{2-[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-2-hydroxy-acetylamino}-3-fluoro-benzoic acid ethyl ester

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Reaction Steps

To a solution of [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid (60 mg, 161 μmol) in CH2Cl2 (0.8 ml) under an argon atmosphere was added pyridine (16 μl, 202 μmol) and thionyl chloride (14 μl, 193 μmol). 4-Amino-3-fluoro-benzoic acid ethyl ester (29 mg, 161 μmol; CAS Reg. No. 73792-12-8) and pyridine (16 μl, 202 μmol) were added and the reaction mixture was stirred at ambient temperature for 48 h. Ice water/25% aqueous HCl solution 1/1 was added and the mixture was extracted three times with CH2Cl2. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give a brown solid which was purified by preparative thick layer chromatography (silica gel, iPrOAc/heptane) to obtain the title compound (9 mg, 16 μmol; 10%) as colorless solid. MS: m/e=554.4 [M+H+].

Provenance & Evidence