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

HRID 2362457Notes

Reaction equation

HRID 2362457 reaction equation
CO[C:3]1[CH:4]=[C:5]([C@H:9]2OC(=O)N[C@@H:10]2C2C=CC=C(C#CC3C=CC=CC=3)C=2)[CH:6]=[CH:7][CH:8]=1.Br[C:30]1[CH:31]=[C:32]([C@@H:37]2[C@@H:41]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=3)[O:40][C:39](=[O:49])[NH:38]2)[C:33]([F:36])=[N:34][CH:35]=1.C1(C#C)C=CC=CC=1>>[F:36][C:33]1[C:32]([C@@H:37]2[C@@H:41]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=3)[O:40][C:39](=[O:49])[NH:38]2)=[CH:31][C:30]([C:10]#[C:9][C:5]2[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=2)=[CH:35][N:34]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 69083418(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-oneHCID 69083956(4R,5R)-4-(5-bromo-2-fluoropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one

Product 1

HCID 69084163(4R,5R)-4-(2-Fluoro-5-(phenylethynyl)pyridin-3-yl)-5-(3-fluorophenyl)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 (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)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9d660c92c85f49f68556488226514c6f
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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