Water → HCID 58910475, compound

HRID 1502646Notes

Reaction equation

HRID 1502646 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[CH: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]=[CH:13][N:12]=[CH:11]2)=[N:8][CH:9]=1)=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 76113BromotrimethylsilaneHCID 58305612265107-80-0

Product 1

HCID 58910475HCID 58910475, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

87 mg (corresponding to 0.462 mmol) of 5-acetyl-2-(1H-imidazole-1-yl)pyridine was dissolved in 3.0 mL of dichloromethane and 193 μL of triethylamine, and then 120 μL (corresponding to 0.924 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 magnesium sulfate. The solvent was distilled off, the resulting residue was dissolved in 3.0 mL of tetrahydrofuran, and 82.2 mg (corresponding to 0.462 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 24.3 mg (corresponding to 0.091 mmol) of 5-(2-bromoacetyl)-2-(1H-imidazole-1-yl)pyridine (FIG. 3, 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 3.0 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-e3f4f847bbb24a7a92a283bae06215e1
Source dataset
uspto-grants-2015_12
Patent number
US09211350B2

Reaction notes

Loading…