Potassium Carbonate → 6-Methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile

HRID 869008Notes

Reaction equation

HRID 869008 reaction equation
Br[C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](C)[CH:7]=1.[C:11]([O-])([O-])=O.[K+].[K+].[N:17]1[NH:18][N:19]=[CH:20][CH:21]=1>CN(C=O)C>[CH3:11][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([N:18]2[N:19]=[CH:20][CH:21]=[N:17]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 675161H-1,2,3-TriazoleHCID 225912183-Bromo-5-methylpyridine-2-carbonitrile

Product 1

HCID 682815826-Methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrileYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 3-bromo-5-methylpicolinonitrile (2.2 g, 11 mmol) in DMF (28 mL) was added K2CO3 (1.7 g, 12 mmol) and 2H-1,2,3-triazole (650 μL, 11 mmol). The mixture was heated to 100° C. for 36 h, cooled to rt and extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (10-100% EtOAc in hexanes) gave the title compound (1 g, 48%).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification via silica gel chromatography (10-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-23f3ea025f9b408e99e94a5c2e41f0a6
Source dataset
uspto-grants-2015_03
Patent number
US08969352B2

Reaction notes

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