Water → HCID 86717665, compound

HRID 1502637Notes

Reaction equation

HRID 1502637 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[N:11]2)=[N:8][CH:9]=1)(=[O:3])[CH3:2].[Br:15][Si](C)(C)C.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]=[N:11]2)=[N:8][CH:9]=1)=[O:3]

Participants

6

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 86717664HCID 86717664, compound

Product 1

HCID 86717665HCID 86717665, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Next, the obtained 5-acetyl-2-(1H-1,2,3-triazole-1-yl)pyridine is dissolved in dichloromethane and triethylamine. The resulting solution is cooled down to about 0° C., and then bromotrimethylsilane is added thereto. This reaction solution is stirred at room temperature for 10-24 hours. Then, the reaction solution is poured into water and extracted with dichloromethane, and the dichloromethane layer is concentrated. The oily substance resulting from concentration is dried sufficiently and dissolved in tetrahydrofuran. This mixture is cooled down to about 0° C., N-bromosuccinimide is added thereto and stirred at room temperature for about 10-60 minutes. After the completion of the reaction, the solvent is distilled off and purified by chromatography, to obtain 5-(2-bromoacetyl)-2-(1H-1,2,3-triazole-1-yl)pyridine (FIG. 1, step 2). The amount of bromotrimethylsilane may be an amount equivalent or more relative to the reaction substrate, and is typically about 2.0 times greater in molar ratio than 5-acetyl-2-(1H-1,2,3-triazole-1-yl)pyridine. In addition, the amount of triethylamine may be an amount that can neutralize hydrobromic acid generated during reaction, and is typically an amount excessive relative to trimethylsilane bromide. The amount of N-bromosuccinimide may be an amount equivalent or more to the reaction substrate, and is preferably about 1.0 time in molar ratio as much as 5-acetyl-2-(1H-1,2,3-triazole-1-yl)pyridine.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationthe dichloromethane layer is concentrated
  3. customThe oily substance resulting from concentration
  4. customis dried sufficiently
  5. dissolutiondissolved in tetrahydrofuran
  6. temperatureThis mixture is cooled down to about 0° C.
  7. additionN-bromosuccinimide is added
  8. stirringstirred at room temperature for about 10-60 minutes
  9. customAfter the completion of the reaction
  10. distillationthe solvent is distilled off
  11. custompurified by chromatography

Sources & evidence

ORD record
ord-5cb8488a79074989b29c5cb2e9e72e61
Source dataset
uspto-grants-2015_12
Patent number
US09211350B2

Reaction notes

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