4-(Bromomethyl)benzonitrile → 4-((4R,5R)-2-Oxo-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-5-yl)benzonitrile

HRID 2362463Notes

Reaction equation

HRID 2362463 reaction equation
F[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[CH:15]=[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.BrCC1C=CC([C:34]#[N:35])=CC=1>>[O:13]=[C:11]1[NH:10][C@H:9]([C:14]2[CH:15]=[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)[C@@H:8]([C:4]2[CH:5]=[CH:6][C:7]([C:34]#[N:35])=[CH:2][CH:3]=2)[O:12]1

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 69081596(4R,5R)-5-(3-Fluorophenyl)-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one

Product 1

HCID 690942894-((4R,5R)-2-Oxo-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-5-yl)benzonitrile

Procedure

Prepared according to the same procedure as (4R,5R)-5-(3-fluorophenyl)-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one, starting with 4-(bromomethyl)benzonitrile. 1H NMR (CDCl3, 500 MHz) δ: 8.80 (d, J=1.8 Hz, 1H), 8.44 (d, J=2.1 Hz, 1H), 7.90 (t, J=2.0 Hz, 1H), 7.75 (d, J=8.5 Hz, 2H), 7.53-7.63 (m, 2H), 7.35-7.48 (m, 5H), 5.39 (d, J=7.3 Hz, 1H), 4.77 (d, J=7.3 Hz, 1H). 13C-NMR (CDCl3, 126 MHz) δ: 158.1, 153.2, 146.8, 141.7, 136.4, 133.3, 133.2, 131.9, 129.4, 128.7, 126.4, 122.0, 121.6, 118.1, 113.6, 94.5, 85.0, 84.5, 62.4, 43.8, 15.0. Mass spec.: 365.9 (MH)+. The sample was further purified by SFC Prep HPLC (Chiralpak AS-H, 20% MeOH in CO2).

Workup

  1. customPrepared
  2. customThe sample was further purified by SFC Prep HPLC (Chiralpak AS-H, 20% MeOH in CO2)

Sources & evidence

ORD record
ord-434c82fb67d74a1a8ee2ab89847ae2f1
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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