HCID 22249579, compound → HCID 22249662, compound

HRID 890221Notes

Reaction equation

HRID 890221 reaction equation
[CH2:1]([CH:3]([N:6]1[C:10]2=[C:11]3[C:18]([CH3:19])=[N:17][N:16]([C:20]4[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=4[Cl:28])[C:12]3=[N:13][C:14]([CH3:15])=[C:9]2[CH2:8][CH2:7]1)[CH2:4][CH3:5])[CH3:2]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH2:1]([CH:3]([N:6]1[C:10]2=[C:11]3[C:18]([CH3:19])=[N:17][N:16]([C:20]4[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=4[Cl:28])[C:12]3=[N:13][C:14]([CH3:15])=[C:9]2[CH:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 22249579HCID 22249579, compound

Product 1

HCID 22249662HCID 22249662, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

1-(1-Ethylpropyl)-4,8-dimethyl-6-(2,4,6-trichlorophenyl)-1,2,3,6-tetrahydropyrazolo[3,4-b]pyrrolo[2,3-d]pyridine (70 mg, 0.160 mmol) was dissolved in toluene (7 mL). Manganese dioxide (700 mg) was added thereto, followed by stirring at 40° C. overnight. The reaction mixture was filtered through Celite and washed with ethyl acetate. The filtrate was evaporated, and the residue was purified by silica gel column chromatogrpahy (5% ethyl acetate/hexane), to give the title compound (48 mg, 0.110 mmol) as white crystals.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with ethyl acetate
  3. customThe filtrate was evaporated
  4. customthe residue was purified by silica gel column chromatogrpahy (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-70a50fc24e444163843d87d9770b63dc
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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