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

HRID 2362442Notes

Reaction equation

HRID 2362442 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:36]2[C@@H:40]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[CH:42]=3)[O:39][C:38](=[O:48])[NH:37]2)[CH:33]=[N:34][CH:35]=1.C1(C#C)C=CC=CC=1>>[F:47][C:43]1[CH:42]=[C:41]([C@H:40]2[O:39][C:38](=[O:48])[NH:37][C@@H:36]2[C:32]2[CH:33]=[N:34][CH:35]=[C:30]([C:10]#[C:9][C:5]3[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=3)[CH:31]=2)[CH:46]=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 69083418(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-oneHCID 69084164(4R,5R)-4-(5-Bromopyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one

Product 1

HCID 69081596(4R,5R)-5-(3-Fluorophenyl)-4-(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-bromopyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one and phenylacetylene. 1H-NMR (CDCl3, 500 MHz) δ 8.78 (bs, 1H), 8.42 (bs, 1H), 7.90 (m, 1H), 7.57 (m, 2H), 7.35-7.45 (m, 4H), 7.02-7.17 (m, 3H), 6.83 (bs, 1H), 5.30 (d, J=7.3, 1H), 4.83 (d, J=7.3, 1H). 13C-NMR (CDCl3, 126 MHz) δ 164.2, 162.2, 158.6, 152.9, 146.9, 139.1 (d, J=7.7), 136.4, 133.7 (br), 131.9, 131.1 (d, J=8.6), 129.3, 128.7, 122.1, 121.6 (d, J=2.9), 116.6 (d, J=21), 113.0 (d, J=23), 94.2, 85.2, 84.9, 62.5. Mass spec.: 359.3 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e1112a1c23ff4c8bb520e9e9a861acc4
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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