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

HRID 2362445Notes

Reaction equation

HRID 2362445 reaction equation
C1([C@H]2OC(=O)N[C@@H]2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[C:20]C3C=CC=CN=3)[CH:14]=2)C=CC=CC=1.Br[C:28]1[CH:29]=[C:30]([C@@H:34]2[C@@H:38]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=3)[O:37][C:36](=[O:46])[NH:35]2)[CH:31]=[N:32][CH:33]=1.C[Si](C#CC1C=CC=CN=1)(C)C>>[F:45][C:41]1[CH:40]=[C:39]([C@H:38]2[O:37][C:36](=[O:46])[NH:35][C@@H:34]2[C:30]2[CH:31]=[N:32][CH:33]=[C:28]([C:20]#[C:19][C:15]3[CH:14]=[CH:13][CH:18]=[CH:17][N:16]=3)[CH:29]=2)[CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 3

HCID 5228592-(Trimethylsilylethynyl)pyridineHCID 69084164(4R,5R)-4-(5-Bromopyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-oneHCID 69084771(4R,5R)-5-Phenyl-4-(2-(pyridin-2-ylethynyl)pyridin-4-yl)oxazolidin-2-one

Product 1

HCID 69082765(4R,5R)-5-(3-Fluorophenyl)-4-(5-(pyridin-2-ylethynyl)pyridin-3-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-(5-bromopyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one and 2-((trimethylsilyl)ethynyl)pyridine. 1H-NMR (CDCl3, 500 MHz) δ 8.80 (bs, 1H), 8.66 (d, J=3.7, 1H), 8.49 (bs, 1H), 7.94 (s, 1H), 7.75 (ddd, J=7.9, 7.6, 1.5, 1H), 7.58 (d, J=7.6, 1H), 7.41 (ddd, J=7.9, 7.9, 5.8, 1H), 7.33 (dd, J=7.3, 5.2, 1H), 7.09 (m, 3H), 6.97 (bs, 1H), 5.29 (d, J=7.6, 1H), 4.84 (d, J=7.3, 1H). 13C-NMR (CDCl3, 126 MHz) δ 164.2, 162.2, 158.4, 153.1, 150.3, 147.6, 142.3, 139.1 (d, J=6.7), 136.9, 136.6, 131.1, 131.0, 127.6, 123.8, 121.6 (d, J=2.9), 116.6 (d, J=21), 113.0 (d, J=23), 104.3, 92.8, 84.8, 62.5. Mass spec.: 360.0 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b8497a4d8f2445f893b63031a83b456e
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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