Pyridine → 4-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-3-fluorobenzonitrile

HRID 1436416Notes

Reaction equation

HRID 1436416 reaction equation
[Cu][C:2]#[N:3].N1C=CC=CC=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([N:22]3[C:26]([CH3:28])([CH3:27])[CH2:25][O:24][C:23]3=[O:29])[S:20][CH:21]=2)=[C:13]([F:30])[CH:12]=1>CC(N(C)C)=O.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>[CH3:27][C:26]1([CH3:28])[CH2:25][O:24][C:23](=[O:29])[N:22]1[C:19]1[S:20][CH:21]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([C:2]#[N:3])=[CH:12][C:13]=2[F:30])[N:18]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 250298763-[4-(4-Bromo-2-fluorophenyl)-1,3-thiazol-2-yl]-4,4-dimethyl-1,3-oxazolidin-2-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 250298784-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-3-fluorobenzonitrileYield 116.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

Copper (I) cyanide (0.09 g, 1.0 mmol) and pyridine (0.17 mL, 1.6 mmol) were added under a nitrogen atmosphere to a solution of 3-[4-(4-bromo-2-fluorophenyl)-1,3-thiazol-2-yl]-4,4-dimethyl-1,3-oxazolidin-2-one (0.4 g, 1.0 mmol), prepared in step 7 of Example 78, and tetrakis(triphenylphosphine)palladium(0) (115 mg, 0.1 mmol) in dimethylacetamide. The reaction solution was sealed and placed in a microwave reactor (200° C./1 h). LC/MS indicated the reaction was complete. The reaction was concentrated under reduced pressure. The residue was purified on silica gel using a stepwise gradient of 1-3% methanol:methylene chloride to give the title compound (370 mg, 55%) as a yellow solid, mp 237° C. (dec.).

Workup

  1. customThe reaction solution was sealed
  2. customplaced in a microwave reactor
  3. custom(200° C./1 h)
  4. concentrationThe reaction was concentrated under reduced pressure
  5. customThe residue was purified on silica gel using a stepwise gradient of 1-3% methanol

Sources & evidence

ORD record
ord-24a987350cab4b44b18654e44e4f5efc
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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