1-Ethynyl-2-fluorobenzene → (4R,5R)-4-(6-((2-Fluorophenyl)ethynyl)pyridin-2-yl)-5-(3-methoxyphenyl)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 optically-enriched (4R,5R)-4-(6-bromopyridin-2-yl)-5-(3-methoxyphenyl)oxazolidin-2-one and 1-ethynyl-2-fluorobenzene. 1H-NMR (CDCl3, 500 MHz) δ 7.81 (dd, J=7.9, 7.6, 1H), 7.63 (ddd, J=7.6, 7.0, 1.2, 1H), 7.60 (d, J=7.6, 1H), 7.41 (m, 2H), 7.36 (dd, J=7.9, 7.9, 1H), 7.18 (m, 2H), 7.05 (m, 2H), 6.94 (m, 1H), 5.89 (bs, 1H), 5.62 (d, J=5.8, 1H), 4.98 (d, J=6.1, 1H), 3.86 (s, 3H). 13C-NMR (CDCl3, 126 MHz) δ 163.1 (d, J=253), 162.1, 160.2, 158.9, 158.6, 143.6, 139.8, 137.7, 134.0, 131.2 (d, J=7.7), 130.2, 127.4, 124.2 (d, J=3.8), 120.1, 117.9, 115.8 (d, J=21), 114.9, 111.0, 93.1, 83.7, 83.5, 64.9, 55.5.

Provenance & Evidence