7-Chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridine → 1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carbonitrile

HRID 885059Notes

Reaction equation

HRID 885059 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[NH:13]1[CH:17]=[N:16][C:15]([C:18]#[N:19])=[N:14]1>N1C=CC=CC=1.CCOC(C)=O.[Cu]I>[CH3:12][O:11][C:5]1[CH:4]=[N:3][C:2]([N:13]2[CH:17]=[N:16][C:15]([C:18]#[N:19])=[N:14]2)=[C:7]2[NH:8][CH:9]=[CH:10][C:6]=12

Participants

6

Reactant 2

HCID 159870137-Chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridineHCID 178510603HCID 178510603, compound

Product 1

HCID 580260371-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carbonitrileYield 38%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

7-Chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridine (4 g, 21.90 mmol), 1H-1,2,4-triazole-3-carbonitrile (6.18 g, 65.7 mmol) and copper (I) iodide (1.252 g, 6.57 mmol) were combined in pyridine (6 mL) in a sealed tube. The mixture was heated to 150° C. for 6 hrs. After cooling to room temperature, the mixture was diluted with EtOAc (3000 mL), washed with 5% NaHCO3 (100 mL), brine (100 mL) and concentrated. The residue was purified by silica gel column using 30% EtOAc in hexanes mixture to give 1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carbonitrile (2 g, 8.33 mmol, 38.0% yield). LCMS: m/z 241.1 (M+H), 1.67 min (method 8).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with 5% NaHCO3 (100 mL), brine (100 mL)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-223b657cd7f14d8ba11728e870fcc519
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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