(4R,5R)-5-(2,5-Difluorophenyl)-4-(2-fluoro-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one → (4R,5R)-5-(2,5-Difluorophenyl)-4-(2-methoxy-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one

HRID 2362461Notes

Reaction equation

HRID 2362461 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:12][C:11](=[O:13])[NH:10][C@@H:9]2[C:14]2[C:15]([O:28][CH3:29])=[N:16][CH:17]=[C:18]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=2)[CH:5]=[CH:6][CH:7]=1.[F:30]C1C=CC(F)=CC=1[C@H]1OC(=O)N[C@@H]1C1C(F)=NC=C(C#CC2C=CC=CC=2)C=1>>[F:30][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[C@H:8]1[O:12][C:11](=[O:13])[NH:10][C@@H:9]1[C:14]1[C:15]([O:28][CH3:29])=[N:16][CH:17]=[C:18]([C:20]#[C:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 69082915(4R,5R)-5-(2,5-Difluorophenyl)-4-(2-fluoro-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-oneHCID 69086137(4R,5R)-5-(3-Fluorophenyl)-4-(2-methoxy-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one

Product 1

HCID 69083515(4R,5R)-5-(2,5-Difluorophenyl)-4-(2-methoxy-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one

Procedure

Prepared according to the same procedure as (4R,5R)-5-(3-fluorophenyl)-4-(2-methoxy-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one, starting with ((4R,5R)-5-(2,5-difluorophenyl)-4-(2-fluoro-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one. 1H NMR (CDCl3) δ: 8.33 (d, J=2.1 Hz, 1H), 7.83 (d, J=1.8 Hz, 1H), 7.50-7.54 (m, 2H), 7.33-7.38 (m, 3H), 7.20-7.25 (m, 1H), 7.03-7.10 (m, 2H), 6.06 (s, 1H), 5.54 (d, J=5.2 Hz, 1H), 4.98 (d, J=5.2 Hz, 1H), 3.88 (s, 3H). 19F NMR (CDCl3) δ: −119.97-115.26 (m, 1F), −123.84 (br. s., 1F). Mass spec.: 407.1 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2ab34ea9947a49778dbbff23151cd81a
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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