1H-1,2,4-Triazole → 4-Methoxy-7-(1,2,4-triazol-1-yl)-6-azaindole

HRID 1783388Notes

Reaction equation

HRID 1783388 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.[OH-].[K+]>CO.[Cu]>[CH3:12][O:11][C:5]1[CH:4]=[N:3][C:2]([N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 14797Potassium HydroxideHCID 159870137-Chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 207912504-Methoxy-7-(1,2,4-triazol-1-yl)-6-azaindoleYield 58%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 7-chloro-4-methoxy-6-azaindole (1.029 g, 5.62 mmol), 1,2,4-triazole (11.6 g, 30 equiv), copper bronze (0.72 g, 11.2 mgatom) and finely pulverized KOH (0.63 g, 11.2 mmol) was heated in a sealed tube at 160° C. (oil bath temperature) for 18 h. The cooled mixture was taken up in MeOH and the resulting slurry was filtered through a pad of Celite. The filtrate was evaporated, the residue taken up in EtOAc and the resulting suspension was filtered. This process was repeated and the resulting solution was susequently adsorbed on silica gel and the volatiles were removed in vacuo. This solid was applied to the top of a silica gel chromatography column, which was eluted with 10-50% EtOAc—CH2Cl2 to give the title compound (0.697 g, 58%) as an off-white solid:

Workup

  1. filtrationthe resulting slurry was filtered through a pad of Celite
  2. customThe filtrate was evaporated
  3. filtrationthe resulting suspension was filtered
  4. customthe volatiles were removed in vacuo
  5. washwas eluted with 10-50% EtOAc—CH2Cl2

Sources & evidence

ORD record
ord-67bc241e82b741dfbd05c329de930cf6
Source dataset
uspto-grants-2009_03
Patent number
US07501419B2

Reaction notes

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