Pyrazole → HCID 23498866, compound

HRID 1836904Notes

Reaction equation

HRID 1836904 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH2:23]Br)=[CH:21][C:20]3[C:19]([CH3:26])([CH3:25])[C:18](=[O:27])[CH2:17][C:16]([CH3:29])([CH3:28])[C:15]=3[CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:30]1[CH:34]=[CH:33][CH:32]=[N:31]1>CN1CCCC1.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[C:13]2[C:22]([CH2:23][N:30]3[CH:34]=[CH:33][CH:32]=[N:31]3)=[CH:21][C:20]3[C:19]([CH3:26])([CH3:25])[C:18](=[O:27])[CH2:17][C:16]([CH3:29])([CH3:28])[C:15]=3[CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 1048PyrazoleHCID 23498955HCID 23498955, compound

Product 1

HCID 23498866HCID 23498866, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 1.0 g (2.2 mmol) of methyl-4-[(E)-2-(5,5,8,8-tetramethyl-3-bromomethyl-6-oxo -5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid and 0.6 g (8.8 mmol) of pyrazole in 15 ml of N-methylpyrrolidine was heated at 100°. After 2 h, the reaction mixture was cooled to room temperature, poured into brine, extracted with ethyl acetate, washed with brine and dried over sodium sulfate. The organic solution was adsorbed onto silica gel and purified by flash chromatography (gradient elution: hexane-18% ethyl acetate/hexane) to afford 0.71 g (73%) of Methyl-4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6-oxo -5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid (MH+=443).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. custompurified by flash chromatography (gradient elution: hexane-18% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1c746336d74140549f1790316c4334b5
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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