7-(2-Chloro-4,6-dimethylphenyl)-2-methyl-3-(1-propyl but-1-enyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine → 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-3-(1-propylbutyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine

HRID 916212Notes

Reaction equation

HRID 916212 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([C:20]([CH2:24][CH2:25][CH3:26])=[CH:21][CH2:22][CH3:23])[N:17]([CH3:19])[N:18]=[C:11]12>C(O)(=O)C.[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([CH:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[N:17]([CH3:19])[N:18]=[C:11]12

Participants

5

Reactant 1

HCID 692923867-(2-Chloro-4,6-dimethylphenyl)-2-methyl-3-(1-propyl but-1-enyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine

Product 1

HCID 221362617-(2-chloro-4,6-dimethylphenyl)-2-methyl-3-(1-propylbutyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridineYield 24.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-(2-Chloro-4,6-dimethylphenyl)-2-methyl-3-(1-propyl but-1-enyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine (41.5 mg) was dissolved in acetic acid (1 mL) and 12 mg of 10% palladium on carbon was added. The mixture was stirred under hydrogen at one atmosphere for 12 h. The mixture was diluted with ethyl acetate and filtered through diatomaceous earth which was then washed with ethyl acetate. The ethyl acetate filtrate was washed with aqueous sodium bicarbonate, dried with magnesium sulfate, and concentrated. The residue was chromatographed on silica gel eluting with an acetone/hexane gradient to provide 10.2 mg of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-3-(1-propylbutyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine, as a crystalline film, ms m/z 374 (MH+).

Workup

  1. filtrationfiltered through diatomaceous earth which
  2. washwas then washed with ethyl acetate
  3. washThe ethyl acetate filtrate was washed with aqueous sodium bicarbonate
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with an acetone/hexane gradient

Sources & evidence

ORD record
ord-10bd3cdb3e814cf487f70a0f35f376aa
Source dataset
uspto-grants-2007_09
Patent number
US07268146B2

Reaction notes

Loading…