Imidazole → HCID 69093736, compound

HRID 2174278Notes

Reaction equation

HRID 2174278 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[C:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[N:12]=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:10]=1>CN(C=O)C>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][N:13]1[C:9]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[N:10][C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:12]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 69094001HCID 69094001, compound

Product 1

HCID 69093736HCID 69093736, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of imidazole (1.2 eq) in DMF was added sodium hydride (2 eq). The reaction generated gas and was stirred for 10 minutes. Then 2-(5-bromo-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)pyridine (I-16) was added. The reaction was stirred at 100° C. for 12 hr. The reaction was quenched with brine, extracted with methylene chloride, dried over sodium sulfate and concentrated. The mixture was purified by SiO2 chromatography to afford 2-(1-(2-fluorobenzyl)-5-(1H-imidazol-1-yl)-1H-1,2,4-triazol-3-yl)pyridine as a solid in 26.7% yield.

Workup

  1. stirringThe reaction was stirred at 100° C. for 12 hr
  2. customThe reaction was quenched with brine
  3. extractionextracted with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe mixture was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-00111178cec747e59db82e16b8332452
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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