Dichloromethane → methyl 3-(1-(4-fluorophenyl)-6-isopropyl-1H-indazol-5-yl)-2,2-dimethylpropanoate

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Reaction Steps

(1-(4-Fluorophenyl)-6-isopropyl-1H-indazol-5-yl)methanol (145 mg, 0.51 mmol) was dissolved in 5 mL of dry DCM and TiCl4 (60 mL of 1.0 M DCM solution, 60 mmol) was added portionwise and then stirred 30 min. Then the reaction was treated with 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (0.2 mL, 1.0 mmol). The reaction was quenched with aqueous sodium bicarbonate and extracted 2×EtOAc, the organic layers dried over MgSO4, filtered, and concentrate. The residue was purified on SiO2 by MPLC using a 5:95 to 10:90 EtOAc/hexane gradient to give 87 mg (47% yield) of methyl 3-(1-(4-fluorophenyl)-6-isopropyl-1H-indazol-5-yl)-2,2-dimethylpropanoate. MS found: (M+H)+=369.

Provenance & Evidence