1-Ethynyl-3-fluorobenzene → (4R,5R)-4-(6-((3-Fluorophenyl)ethynyl)pyridin-2-yl)-5-(3-methoxyphenyl)oxazolidin-2-one

HRID 2362439Notes

Reaction equation

HRID 2362439 reaction equation
COC1C=C([C@H]2OC(=O)N[C@@H]2C2C=CC=C(C#CC3C=CC=CC=3)C=2)C=CC=1.Br[C:30]1[N:35]=[C:34]([C@@H:36]2[C@@H:40]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([O:47][CH3:48])[CH:42]=3)[O:39][C:38](=[O:49])[NH:37]2)[CH:33]=[CH:32][CH:31]=1.[C:50]([C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([F:58])[CH:53]=1)#[CH:51]>>[F:58][C:54]1[CH:53]=[C:52]([C:50]#[C:51][C:30]2[N:35]=[C:34]([C@@H:36]3[C@@H:40]([C:41]4[CH:46]=[CH:45][CH:44]=[C:43]([O:47][CH3:48])[CH:42]=4)[O:39][C:38](=[O:49])[NH:37]3)[CH:33]=[CH:32][CH:31]=2)[CH:57]=[CH:56][CH:55]=1

Participants

4

Reactant 3

HCID 5202181-Ethynyl-3-fluorobenzeneHCID 69083418(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-oneHCID 86673405(4R,5R)-4-(6-bromopyridin-2-yl)-5-(3-methoxyphenyl)oxazolidin-2-one

Product 1

HCID 70945836(4R,5R)-4-(6-((3-Fluorophenyl)ethynyl)pyridin-2-yl)-5-(3-methoxyphenyl)oxazolidin-2-one

Procedure

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.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9b0149fdc55849ad81b23287775f2dbe
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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