Potassium Carbonate → HCID 70115051, compound

HRID 868935Notes

Reaction equation

HRID 868935 reaction equation
[N:1]1[N:2]=[C:3]([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[NH:4][CH:5]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:4]2[CH:5]=[N:1][N:2]=[C:3]2[C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178420012HCID 178420012, compound

Product 1

HCID 70115051HCID 70115051, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4H-1,2,4-triazol-3-yl)pyridine (0.56 g, 3.8 mmol), PMBCl (0.66 g, 4.2 mmol), and K2CO3 (2.12 g, 15.3 mmol) in DMF (10 mL) was stirred for 4 h at room temperature. The reaction mixture was then diluted with water and extracted with DCM. The combined organic layers were washed with water three times, dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography to give 4-(4-(4-methoxybenzyl)-4H-1,2,4-triazol-3-yl)pyridine (0.60 g).

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with water three times
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-30063e7c4cf94e55a910c8bee26f97fd
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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