Boron trifluoride etherate → methyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)-2,2-dimethylpropanoate

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Reaction Steps

(1-(4-Fluorophenyl)-6-methyl-1H-indazol-5-yl)methanol (178 mg, 0.51 mmol) was dissolved in 5 mL of dry DCM and BF3—OEt2 (0.09 mL, 0.7 mmol) was added portionwise and then stirred 30 min. Then the reaction was treated with 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (0.43 mL, 2.1 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 1:9 gradient to give 121 mg (51% yield) of methyl 3-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)-2,2-dimethylpropanoate. MS found: (M+H)+=341.

Provenance & Evidence