Isopropanol → trans-2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehyde

HRID 1639754Notes

Reaction equation

HRID 1639754 reaction equation
[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][OH:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.C[N+]1([O-])CCOCC1.CC(O)C>C(#N)C.C(OCC)(=O)C>[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH:13]=[O:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 82029Methyl morpholine oxideHCID 66720627Trans-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanol

Product 1

HCID 86641921trans-2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehydeYield 82%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trans-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanol (2000 mg, 9.89 mmol), 4 Å molecular sieves (800 mg), 4-methylmorpholine N-oxide (1.74 g, 14.8 mmol) and tetra-n-propylammonium perruthenate(VII) (174 mg, 0.494 mmol) were dissolved in acetonitrile (100 mL), and the mixture was stirred at room temperature for 2 hr. 2-Propanol was added and the mixture was stirred for 30 min, diluted with ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.62 g, yield 82%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washwashed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b00a67482dc14228a427cada17e7c6b5
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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