Phenylacetylene → (4R,5R)-4-(2-Fluoro-5-(phenylethynyl)pyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one

Participants

Reaction Steps

Prepared according to the same procedure as (+)-(4R,5R)-5-(3-methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one, starting with (4R,5R)-4-(5-bromo-2-fluoropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one and phenylacetylene. 1H NMR (CDCl3) δ: 8.39 (d, J=0.9 Hz, 1H), 8.11 (dd, J=9.0, 2.0 Hz, 1H), 7.56 (dd, J=7.8, 1.7 Hz, 2H), 7.35-7.46 (m, 4H), 7.07-7.22 (m, 3H), 6.77 (s, 1H), 5.37 (d, J=5.2 Hz, 1H), 5.04 (d, J=5.2 Hz, 1H). 19F NMR (CDCl3) δ: −70.65 (d, J=13.0 Hz, 1F), −111.45 (br. s., 1F). 13C NMR (CDCl3) δ: 163.2, 158.8, 159.6, 150.5, 140.8, 139.8, 131.8, 131.0, 129.3, 128.7, 122.0, 121.2, 121.2, 119.8, 116.6, 112.7, 93.8, 84.0, 83.6, 58.0. Mass spec.: 377.2 (MH)+.

Provenance & Evidence