Imidazole → HCID 20330254, compound

HRID 1862837Notes

Reaction equation

HRID 1862837 reaction equation
Br[CH:2]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[N:11]=1)[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.C1CCN2C(=NCCC2)CC1>CC(C)=O>[F:16][C:12]1[N:11]=[C:10]([O:9][CH:2]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20330253HCID 20330253, compound

Product 1

HCID 20330254HCID 20330254, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 14.5 g (0.05 mole) of 1-bromo-1-(6-fluoro-2-pyridinyloxy)-3,3-dimethyl-2-butanone in 75 ml acetone cooled to -10° C. was added 3.4 g (0.05 mole) imidazole. Then, 7.61 g (0.05 mole) of 1,5-diaza(5.4.0)undec-5-ene was added dropwise. After the addition was complete, the mixture was stirred for 30 minutes at 0° C. and the solvent evaporated. Water was added to the residue and the mixture extracted with diethyl ether. The ether extract was dried using magnesium sulfate and the solvent evaporated. Chromatography on silica gel (8:2 hexane:acetone) gave 6.3 g (55% yield) of 1-(6-fluoro-2-pyridinyloxy)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanone. Recrystallization from hexane gave product melting at 90°-93° C.

Workup

  1. additionAfter the addition
  2. customthe solvent evaporated
  3. additionWater was added to the residue
  4. extractionthe mixture extracted with diethyl ether
  5. extractionThe ether extract
  6. customwas dried
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-85639b81b027445bbcd85d6485890b9a
Source dataset
uspto-grants-1979_09
Patent number
US04166854

Reaction notes

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