Water → Racemic 4-{2-[2-oxo-4-(trifluoromethyl)-1,3-oxazolidin-3-yl]-1,3-thiazol-4-yl}benzonitrile

HRID 1436395Notes

Reaction equation

HRID 1436395 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[CH:17]([C:18]([F:21])([F:20])[F:19])[CH2:16][O:15][C:14]3=[O:22])[S:11][CH:12]=2)=[CH:4][CH:3]=1.O.[CH3:24][N:25](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:22]=[C:14]1[N:13]([C:10]2[S:11][CH:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:24]#[N:25])=[CH:3][CH:4]=3)[N:9]=2)[CH:17]([C:18]([F:21])([F:20])[F:19])[CH2:16][O:15]1

Participants

7

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 250296343-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-4-(trifluoromethyl)-1,3-oxazolidin-2-one

Product 1

HCID 69072927Racemic 4-{2-[2-oxo-4-(trifluoromethyl)-1,3-oxazolidin-3-yl]-1,3-thiazol-4-yl}benzonitrileYield 72%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

3-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-4-(trifluoromethyl)-1,3-oxazolidin-2-one, prepared in step 3 of Example 64, (0.455 g, 1.15 mmol) and zinc cyanide (81 mg, 0.69 mmol) were dissolved in 12 mL of DMF. The mixture was purged with nitrogen for 15 min and then tetrakis(triphenylphosphine)palladium(0) (66.5 mg, 0.058 mmol) was added and the mixture was heated to 120° C. for 1.5 h. The mixture was cooled and diluted with ethyl acetate and poured into 200 mL of water. The mixture was extracted with ethyl acetate, the organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (gradient 1% acetone/hexane to 10% acetone/hexane) afforded racemic 4-{2-[2-oxo-4-(trifluoromethyl)-1,3-oxazolidin-3-yl]-1,3-thiazol-4-yl}benzonitrile (278 mg, 72%) as a white solid.

Workup

  1. customThe mixture was purged with nitrogen for 15 min
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ee7db213cb74b6b8abc7d844cf26939
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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