3-(Trimethylsilylethynyl)pyridine → (4R,5R)-5-Phenyl-4-(2-(pyridin-3-ylethynyl)pyridin-4-yl)oxazolidin-2-one

HRID 2362444Notes

Reaction equation

HRID 2362444 reaction equation
[C:1]1([C@H:7]2[O:11][C:10](=[O:12])[NH:9][C@@H:8]2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[C:20]C3C=CC=CN=3)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:28]1[CH:33]=[C:32]([C@@H]2[C@@H](C3C=CC=CC=3)OC(=O)N2)[CH:31]=[CH:30][N:29]=1.C[Si](C#CC1C=NC=CC=1)(C)C>>[C:1]1([C@H:7]2[O:11][C:10](=[O:12])[NH:9][C@@H:8]2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[C:20][C:33]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 41008573-(Trimethylsilylethynyl)pyridineHCID 69084771(4R,5R)-5-Phenyl-4-(2-(pyridin-2-ylethynyl)pyridin-4-yl)oxazolidin-2-oneHCID 86673413(4R,5R)-4-(2-Bromopyridin-4-yl)-5-phenyloxazolidin-2-one

Product 1

HCID 69093406(4R,5R)-5-Phenyl-4-(2-(pyridin-3-ylethynyl)pyridin-4-yl)oxazolidin-2-one

Procedure

Prepared according to the same procedure as (4R,5R)-5-phenyl-4-(2-(pyridin-2-ylethynyl)pyridin-4-yl)oxazolidin-2-one, starting with (4R,5R)-4-(2-bromopyridin-4-yl)-5-phenyloxazolidin-2-one and 3-((trimethylsilyl)ethynyl)pyridine. 1H-NMR (CDCl3, 500 MHz) δ 8.82 (bs, 1H), 8.67 (bs, 1H), 7.90 (d, J=7.6, 1H), 7.55 (bs, 1H), 7.30-7.51 (m, 6H), 7.21 (d, J=4.0, 1H), 6.94 (bs, 1H), 5.24 (d, J=7.0, 1H), 4.84 (d, J=7.0, 1H). 13C-NMR (CDCl3, 126 MHz) δ 158.9, 151.1, 148.3, 143.9, 139.0, 136.6, 129.8, 129.4, 126.1, 124.6, 120.8, 91.3, 86.9, 85.3, 63.7. Mass spec.: 342.0 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f97de3182ef14bff806e1af092e5ef32
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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