Tetrapropylammonium → HCID 86602413, compound

HRID 2373238Notes

Reaction equation

HRID 2373238 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]=[C:10]3[N:22]([CH2:25][CH3:26])[N:23]=[CH:24][C:9]=23)=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[O:15])=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]=[C:10]3[N:22]([CH2:25][CH3:26])[N:23]=[CH:24][C:9]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 11545088HCID 11545088, compound

Product 1

HCID 86602413HCID 86602413, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [4-(6-chloro-3-pyridyl)-1-ethyl-6-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (730 mg), 4-methylmorpholine N-oxide (352 mg) in DCM (20 ml) was added tetrapropylammonium perrutenate (70.3 mg) at room temperature and the mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered through celite pad. The filtrate was washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3, water, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of MeOH and CHCl3 (1:10) to give 4-(6-chloro-3-pyridyl)-1-ethyl-6-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (660 mg) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite pad
  2. washThe filtrate was washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3, water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of MeOH and CHCl3 (1:10)

Sources & evidence

ORD record
ord-111171673b374a418ddbb44aa2feb9c9
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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