Dimethylformamide → 7-Phenylthio-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole

HRID 2084284Notes

Reaction equation

HRID 2084284 reaction equation
Br[CH:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[N:8]=[C:7]([CH3:17])[C:6]=2[C:5](=[O:18])[CH2:4][C:3]1([CH3:20])[CH3:19].[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26]([O-])=O.[Na+].[CH3:30]N(C)C=O>[Cl-].[Na+].O>[C:22]1([S:26][CH:2]2[C:10]3[N:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)[N:8]=[C:7]([CH3:17])[C:6]=3[C:5](=[O:18])[CH2:4][C:3]2([CH3:20])[CH3:19])[CH:30]=[CH:21][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 40739867-Bromo-3,6,6-trimethyl-1-pyridin-2-yl-5,7-dihydroindazol-4-oneHCID 23672340Sodium 2-thenoate

Product 1

HCID 98204247-Phenylthio-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazoleYield 45%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

The solution of 7-bromo-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole (0.6 g, 1.8 mmol), prepared as described in example 4, and sodium thiophenate (0.3 g, 2.24 mmol) in dry N,N-dimethylformamide (10 ml) was stirred at room temperature for about 5 hours and then poured into brine and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate end evaporated. The residue was chromatographed on silica gel (cyclohexane:ethyl acetate=90:10) to give 0.3 g (45% yield) of the title compound as a colourless solid which crystallized on standing.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate end
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (cyclohexane:ethyl acetate=90:10)

Sources & evidence

ORD record
ord-dba86186f0bb4c3aac923286a6fe568d
Source dataset
uspto-grants-2004_04
Patent number
US06716856B1

Reaction notes

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