1-Ethynyl-3-fluorobenzene → (4R,5R)-4-(6-((3-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-3-fluorobenzene. 1H-NMR (CDCl3, 500 MHz) δ 7.81 (d, J=7.9, 7.6, 1H), 7.57 (dd, J=7.9, 0.6, 1H), 7.30-7.45 (M, 5H), 7.13 (m, 1H), 7.04 (m, 2H), 6.95 (m, 1H), 6.00 (bs, 1H), 5.62 (d, J=6.1, 1H), 4.97 (dd, J=5.8, 0.6, 1H), 3.86 (s, 3H). 13C-NMR (CDCl3, 126 MHz) δ 162.5 (d, J=248), 160.2, 159.0, 158.6, 143.5, 139.7, 137.8, 130.20 (d, J=8.6), 130.19, 128.1 (d, J=2.9), 127.4, 123.9 (d, J=10), 120.1, 119.0 (d, J=23), 117.9, 116.8 (d, J=21), 114.8, 111.2, 89.0, 88.7 (d, J=3.8), 83.7, 64.9, 55.5.

Provenance & Evidence