Dimethylformamide → (E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate

Participants

Reaction Conditions

Reaction Steps

Trimethylphosphonoacetate (2.4 g, 13.4 mmol) was dissolved in 15 mL anhydrous DMF and treated with sodium hexadimethylsilazane (13.4 mmol, 1 M in THF). (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone (1.63 g, 5.16 mmol) was added and the reaction was heated to 85° C. for 16 hours. The following day, the cooled reaction was extracted from brine using ether×3 and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel using 25% EtOAc in hexanes to give 1.74 g (91%) of (E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate as a clear oil. MS found: (M+H)+=373.

Provenance & Evidence