Water → HCID 86717667, compound

HRID 1502643Notes

Reaction equation

HRID 1502643 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[N:14]=[CH: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[N:14]=[CH:13][CH:12]=[N:11]2)=[N:8][CH:9]=1)=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 76113BromotrimethylsilaneHCID 86717666HCID 86717666, compound

Product 1

HCID 86717667HCID 86717667, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

31.9 mg (corresponding to 0.170 mmol) of 5-acetyl-2-(2H-1,2,3-triazole-2-yl)pyridine was dissolved in 1.0 mL of dichloromethane and 71 μL of triethylamine, and then 44.1 μL (corresponding to 0.51 mmol) of bromotrimethylsilane was dropped under ice cooling. The resulting solution was stirred over night at room temperature under argon gas atmosphere, and then, the reaction solution was 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 anhydrous magnesium sulfate. The solvent was distilled off, the resulting residue was dissolved in 1.0 mL of tetrahydrofuran, and 33.3 mg (corresponding to 0.17 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 20.2 mg (corresponding to 0.076 mmol) of 5-(2-bromoacetyl)-2-(2H-1,2,3-triazole-2-yl)pyridine (FIG. 2, 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 anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. dissolutionthe resulting residue was dissolved in 1.0 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-0e34e8c02dec4040865aaef18b6549cf
Source dataset
uspto-grants-2015_12
Patent number
US09211350B2

Reaction notes

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