4-Fluorophenylboronic acid → 2-(3,5-Dichloro-4'-fluoro-biphenyl-4-ylmethyl)-2-aza-spiro[4.5]decan-1-one

Participants

Reaction Conditions

Reaction Steps

Purged with N2 a mixture of 2-(4-bromo-2,6-dichloro-benzyl)-2-aza-spiro[4.5]decan-1-one (0.091 g, 0.23 mmol) and 4-fluorophenylboronic acid (0.097 g, 0.69 mmol) in toluene (6 mL) and 2M sodium carbonate (0.8 mL). Treat the reaction with Pd(PPh3)4 (0.013 g, 0.011 mmol) and heat to 90° C. for 2 hours under N2. Cool the reaction and dilute with ethyl acetate, and then wash with 1N HCl and water. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product. Purify with a 0 to 100% ethyl acetate in hexanes gradient on silica gel to afford 0.096 g (100%) of the titled product. Rf=0.25 (3/1 hexanes/ethyl acetate). MS (m/z): 406 (M+).

Provenance & Evidence