Tetrahydro-4H-pyran-4-one → 4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-ol

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Reaction Steps

1-(4-Fluorophenyl)-5-iodo-1H-indazole (350 mg, 1.0 mmol) was dissolved in 10 mL dry THF and treated with isopropylmagnesium bromide (1.6 mL of 1 M THF solution) and then BuLi (1.6 M in hexanes, 0.72 mmol, 1.1 mmol) at room temp. After 30 min, tetrahydro-4H-pyran-4-one (270 mg, 2.7 mmol) was added. After 2 h, the reaction was quenched with water, then 1 M HCl, and extracted 2× EtOAc. The organic layers were dried over MgSO4, filtered, concentrated, and the residue was purified using 1:1 EtOAc/hexanes to give 125 mg (39%) of 4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-ol as a clear oil that solidified upon standing. (M+H)+=313.

Provenance & Evidence