2-[4-(2-Fluoro-5-iodo-4-methoxyphenyl)piperidin-1-yl]-2-oxoethyl acetate → HCID 86630549, compound

Participants

Reaction Steps

A mixture of 2-[4-(2-fluoro-5-iodo-4-methoxyphenyl)piperidin-1-yl]-2-oxoethyl acetate (Step A; 33 mg; 0.076 mmol) and (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (Intermediate 9; 68 mg, 0.114 mmol) was treated with 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (˜5 mg) as described earlier. The product was purified by chiral HPLC (ChiralPak IA column, 15% IPA/heptane) to afford 2-{4-[2′-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-fluoro-6-methoxy-4′-(trifluoromethyl)biphenyl-3-yl]piperidin-1-yl}-2-oxoethyl acetate as a colorless glass. LCMS=779.0 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers) δ 7.86 (s, 1 H), 7.69 (s, 2 H), 7.68-7.60 (m, 2 H), 7.32 (d, J=7.8 Hz, 1 H), 6.96-6.91 (m, 1 H), 6.72 (dd, J=11.9, 2.1 Hz, 1 H), 5.59-5.54 (m, 1 H), 4.90 (d, J=15.6 Hz, 1 H), 4.80-4.65 (m, 3 H), 4.13-4.04 (m, 1 H), 3.88-3.72 (m, 2 H), 3.78 (s, 3H), 3.21-3.04 (m, 2H), 2.72-2.67 (m, 1H), 2.17 (s, 3H), 1.96-1.83 (m, 2 H), 1.70-1.59 (m, 2 H), 0.42-0.39 (m, 3 H)

Provenance & Evidence