Phenylacetylene → (4R,5R)-5-Phenyl-4-(2-(phenylethynyl)pyridin-4-yl)oxazolidin-2-one

HRID 2362441Notes

Reaction equation

HRID 2362441 reaction equation
CO[C:3]1[CH:4]=[C:5]([C@H:9]2[O:13][C:12](=[O:14])[NH:11][C@@H:10]2[C:15]2[CH:20]=[CH:19]C=[C:17]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)[CH:6]=[CH:7][CH:8]=1.BrC1C=C([C@@H]2[C@@H](C3C=CC=CC=3)OC(=O)N2)C=C[N:31]=1.C1(C#C)C=CC=CC=1>>[C:5]1([C@H:9]2[O:13][C:12](=[O:14])[NH:11][C@@H:10]2[C:15]2[CH:20]=[CH:19][N:31]=[C:17]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)[CH:4]=[CH:3][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 69083418(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-oneHCID 86673413(4R,5R)-4-(2-Bromopyridin-4-yl)-5-phenyloxazolidin-2-one

Product 1

HCID 69093438(4R,5R)-5-Phenyl-4-(2-(phenylethynyl)pyridin-4-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-(2-bromopyridin-4-yl)-5-phenyloxazolidin-2-one and phenylacetylene. 1H-NMR (CDCl3, 500 MHz) δ 8.64 (d, J=4.9, 1H), 7.60 (m, 2H), 7.50 (m, 1H), 7.45 (m, 3H), 7.40 (m, 3H), 7.34 (m, 2H), 7.17 (dd, J=5.2, 1.5, 1H), 6.73 (bs, 1H), 5.25 (d, J=7.3, 1H), 4.82 (d, J=7.3, 1H). 13C-NMR (CDCl3, 126 MHz) δ 158.8, 151.0, 148.1, 144.6, 136.7, 132.2, 129.7, 129.4, 129.3, 128.6, 126.2, 124.4, 121.9, 120.2, 90.5, 88.2, 85.4, 63.7. Mass spec.: 341.2 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f8d52143cb6849a4bc2283384a43a12a
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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