Water → HCID 86717668, compound

HRID 1502649Notes

Reaction equation

HRID 1502649 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[N:8][CH:9]=1)(=[O:3])[CH3:2].[Br:15][Si](C)(C)C.O.BrN1C(=O)CCC1=O>ClCCl.C(N(CC)CC)C>[Br:15][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[N:8][CH:9]=1)=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 76113BromotrimethylsilaneHCID 53632732HCID 53632732, compound

Product 1

HCID 86717668HCID 86717668, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

480 mg (corresponding to 2.55 mmol) of 5-acetyl-2-(1H-1,2,4-triazole-1-yl)pyridine was dissolved in 10 mL of dichloromethane and 1.07 mL of triethylamine, and then 662 μL (corresponding to 5.10 mmol) of bromotrimethylsilane was dropped under ice cooling. The resulting solution was stirred over night at room temperature under argon gas atmosphere, and then supplemented with water and extracted 3 times with dichloromethane. The combined dichloromethane layer was washed with water and a saturated saline solution, and dried over magnesium sulfate. The solvent was distilled off, the resulting residue was dissolved in 10 mL of tetrahydrofuran, and 454 mg (corresponding to 2.55 mmol) of N-bromosuccinimide was added thereto under ice cooling. The resulting solution was stirred at room temperature for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by flash silica gel column chromatography (elution solvent: dichloromethane/ethyl acetate=2/1), to obtain 657 mg (corresponding to 2.46 mmol) of 5-(2-bromoacetyl)-2-(1H-1,2,4-triazole-1-yl)pyridine (FIG. 4, step 2).

Workup

  1. extractionextracted 3 times with dichloromethane
  2. washThe combined dichloromethane layer was washed with water
  3. dry with materiala saturated saline solution, and dried over magnesium sulfate
  4. distillationThe solvent was distilled off
  5. dissolutionthe resulting residue was dissolved in 10 mL of tetrahydrofuran
  6. stirringThe resulting solution was stirred at room temperature for 30 minutes
  7. customAfter the completion of the reaction
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was purified by flash silica gel column chromatography (elution solvent: dichloromethane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-140b324510ed4b0aa947495ea07a215c
Source dataset
uspto-grants-2015_12
Patent number
US09211350B2

Reaction notes

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