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

HRID 2362438Notes

Reaction equation

HRID 2362438 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][C:55]([F:58])=[CH:54][CH:53]=1)#[CH:51]>>[F:58][C:55]1[CH:56]=[CH:57][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:53][CH:54]=1

Participants

4

Reactant 3

HCID 5226271-Ethynyl-4-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 70945611(4R,5R)-4-(6-((4-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-4-fluorobenzene. 1H-NMR (CDCl3, 500 MHz) δ 7.79 (dd, J=7.9, 7.6, 1H), 7.61 (m, 2H), 7.54 (d, J=7.6, 1H), 7.36 (m, 2H), 7.10 (m, 2H), 7.04 (m, 2H), 6.94 (m, 1H), 6.40 (bs, 1H), 5.62 (d, J=5.8, 1H), 4.98 (d, J=5.8, 1H), 3.85 (s, 3H). 13C-NMR (CDCl3, 126 MHz) δ 163.2 (d, J=251), 160.1, 158.9, 143.7, 139.8, 137.7, 134.2 (d, J=7.7), 130.2, 127.2, 120.0, 117.9, 116.0 (d, J=23), 114.8, 111.2, 89.1, 88.1, 83.7, 64.9, 55.5. Mass spec.: 389.17 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7986071fff004772971c7a1f9966c514
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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