Dichloromethane → 5-(5-Bromopyridin-3-YL)oxazole

HRID 2406707Notes

Reaction equation

HRID 2406707 reaction equation
C1(C)C(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=CC=1.N12CCCN=C1CCCCC2.ClCCl.[Br:28][C:29]1[CH:30]=[C:31]([CH:35]=[O:36])[CH:32]=[N:33][CH:34]=1>O>[Br:28][C:29]1[CH:30]=[C:31]([C:35]2[O:36][CH:12]=[N:11][CH:10]=2)[CH:32]=[N:33][CH:34]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 53627694Toluenesulfonylmethyl isocyanide

Product 1

HCID 670559205-(5-Bromopyridin-3-YL)oxazoleYield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Toluenesulfonylmethylisocyanide (126 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (122 mg) were added to a dichloromethane (4 ml) solution containing 5-bromo-3-pyridinecarboxaldehyde (100 mg) at room temperature, followed by stirring for 5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 5:2), and a white solid of 5-(5-bromopyridin-3-yl)oxazole (96 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 5:2)

Sources & evidence

ORD record
ord-11789915ec3742aa93885f967d20ee2b
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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