Potassium Carbonate → HCID 86711896, compound

HRID 1475200Notes

Reaction equation

HRID 1475200 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([CH2:19]Cl)[CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:12][C:13]1[CH:18]=[C:17]([CH2:19][N:6]2[C:2]([CH3:1])=[N:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5]2)[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10464537ethyl 3-methyl-1H-1,2,4-triazole-5-carboxylateHCID 111265732-Chloro-4-(chloromethyl)pyridine

Product 1

HCID 86711896HCID 86711896, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate (50 mg, 0.28 mmol) and 2-chloro-4-(chloromethyl)pyridine (50 mg, 0.31 mmol) in DMF (2 mL), K2CO3 (116 mg, 0.84 mmol) was added. The mixture was stirred at RT overnight, and was then diluted with H2O (20 mL), extracted with EtOAc (3×20 mL), 4:1 CHCl3:iPrOH (3×20 mL), dried with MgSO4 and concentrated under reduced pressure. The crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12% to 100% EtOAc) to afford ethyl 1-((2-chloropyridin-4-yl)methyl)-5-methyl-1H-1,2,4-triazole-3-carboxylate (29 mg, 40%) as a white solid. MS (ES+) C12H13ClN4O2 requires: 280 found: 281[M+H]+.

Workup

  1. extractionextracted with EtOAc (3×20 mL), 4:1 CHCl3
  2. dry with materialiPrOH (3×20 mL), dried with MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12% to 100% EtOAc)

Sources & evidence

ORD record
ord-73c322b85f1b4a689a19d927322851d2
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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