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

HRID 2362446Notes

Reaction equation

HRID 2362446 reaction equation
C1([C@H]2OC(=O)N[C@@H]2C2C=CN=C(C#CC3C=CC=CN=3)C=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:51]#[C:52][C:53]1[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=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:51]#[C:52][C:53]3[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=3)[CH:29]=2)[CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 3

HCID 41008573-(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 69086281(4R,5R)-5-(3-Fluorophenyl)-4-(5-(pyridin-3-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 3-((trimethylsilyl)ethynyl)pyridine. 1H-NMR (CDCl3, 500 MHz) δ 8.10-9.50 (bm, 3H), 7.94 (s, 1H), 7.88 (d, J=7.9, 1H), 7.42 (m, 2H), 7.10 (m, 3H), 6.81 (bs, 1H), 5.31 (d, J=7.3, 1H), 4.85 (d, J=7.3, 1H). 13C-NMR (CDCl3, 126 MHz) δ 164.2, 162.2, 158.4, 152.9, 147.4, 139.1 (d, J=6.7), 138.7, 136.5, 132.1 (d, J=11), 131.13, 131.06, 128.6 (d, J=12), 121.5 (d, J=3.8), 116.7 (d, J=21), 113.0 (d, J=23), 90.8, 88.5, 84.8, 62.5. Mass spec.: 360.0 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-98cd21d0174e44908a5b271411db1853
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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