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Sodium hydride → (4S,5R)-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

HRID 1508591
Notes
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Reaction equation

HRID 1508591 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:12]2[O:16][C:15](=[O:17])[NH:14][C@H:13]2[CH3:18])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].[Na+].[Br:21][C:22]1[C:23]([CH2:29]Br)=[N:24][C:25]([Cl:28])=[CH:26][CH:27]=1>C1COCC1>[Br:21][C:22]1[C:23]([CH2:29][N:14]2[C@@H:13]([CH3:18])[C@@H:12]([C:4]3[CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=[C:2]([F:1])[CH:3]=3)[O:16][C:15]2=[O:17])=[N:24][C:25]([Cl:28])=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 232499153-Bromo-2-(bromomethyl)-6-chloropyridine2×HCID 68080296(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one2×

Product 1

HCID 86704638(4S,5R)-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a cold (ice/methanol bath) mixture of (4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 93) (5000 mg, 19.00 mmol) in THF (100 ml) was added sodium hydride (912 mg, 22.80 mmol) all at once. The resulting mixture was stirred cold (ice bath) for 1.5 hrs followed by addition of 3-bromo-2-(bromomethyl)-6-chloropyridine (INTERMEDIATE 30) (5963 mg, 20.90 mmol). The reaction mixture was allowed to slowly warm to ambient in 3 hrs. The reaction was cooled (ice bath) and quenched by HCl (1N, aq.). The resulting mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated under reduced pressure to afford an oil. This oil was purified by flash chromatography (SiO2, Biotage 65i cartridge). The column was eluted by an ethyl acetate/hexanes mixture (0% to 40% ethyl acetate). Related fractions were pooled and concentrated in vacuo to afford a light amber gum of 8.2522 g as the titled compound. LCMS calc.=465.97. found=468.91.

Workup

  1. temperatureto slowly warm
  2. waitto ambient in 3 hrs
  3. temperatureThe reaction was cooled (ice bath)
  4. customquenched by HCl (1N, aq.)
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto afford an oil
  10. customThis oil was purified by flash chromatography (SiO2, Biotage 65i cartridge)
  11. washThe column was eluted by an ethyl acetate/hexanes mixture (0% to 40% ethyl acetate)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d962354bbe6e46bb8af6c0e3192307aa
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221834B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes