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

HRID 2362460Notes

Reaction equation

HRID 2362460 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]=[C:46]([F:48])[CH:45]=[CH:44][C:43]=3[F:49])[O:40][C:39](=[O:50])[NH:38]2)[C:33]([F:36])=[N:34][CH:35]=1.C1(C#C)C=CC=CC=1>>[F:49][C:43]1[CH:44]=[CH:45][C:46]([F:48])=[CH:47][C:42]=1[C@H:41]1[O:40][C:39](=[O:50])[NH:38][C@@H:37]1[C:32]1[C:33]([F:36])=[N:34][CH:35]=[C:30]([C:10]#[C:9][C:5]2[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=2)[CH:31]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 69082811(4R,5R)-4-(5-Bromo-2-fluoropyridin-3-yl)-5-(2,5-difluorophenyl)oxazolidin-2-oneHCID 69083418(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one

Product 1

HCID 69082915(4R,5R)-5-(2,5-Difluorophenyl)-4-(2-fluoro-5-(phenylethynyl)pyridin-3-yl)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-(2,5-difluorophenyl)oxazolidin-2-one and phenylacetylene. 1H NMR (CDCl3) δ: 8.37 (d, J=1.2 Hz, 1H), 8.11 (dd, J=8.9, 2.1 Hz, 1H), 7.56 (dd, J=7.6, 1.8 Hz, 2H), 7.35-7.42 (m, 3H), 7.21-7.26 (m, 1H), 7.07-7.14 (m, 2H), 6.99 (s, 1H), 5.57 (d, J=5.8 Hz, 1H), 5.07 (d, J=5.8 Hz, 1H). 19F NMR (CDCl3) δ: −71.32 (br. s., 1F), −117.12 (br. s., 1F), −123.54 (d, J=8.7 Hz, 1F). Mass spec.: 395.1 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6e97981742e742dfbacc31256f9606d5
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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