tert-Butanol → HCID 59278493, compound

HRID 1698247Notes

Reaction equation

HRID 1698247 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=1)=C.N1C(C)=CC=CC=1C.C([OH:43])(C)(C)C.I([O-])(=O)(=O)=O.[Na+]>O1CCOCC1.O.CCOC(C)=O.[Os](=O)(=O)(=O)=O>[CH:1]([C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=1)=[O:43]

Participants

9

Reactant 4

HCID 6386tert-ButanolHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 58222747HCID 58222747, compound

Product 1

HCID 59278493HCID 59278493, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-vinyl-pyridin-4-yl)-propyl]amide (200 mg, 0.5 mmol) in dioxane (10 mL) and water (3.3 mL) was treated with 2,6-lutidine (116 μL, 1 mmol), 2.5% osmium tetroxide in tert-butanol (125 μL, 0.01 mmol), and sodium periodate (426 mg, 2 mmol). After 5 hours, the reaction mixture was diluted with water (5 mL) and EtOAc (20 mL) and filtered. The organic layer was separated and washed with brine, dried over MgSO4, filtered and concentrated. The mixture was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in heptane to afford 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-formyl-pyridin-4-yl)-propyl]-amide as a white solid.

Workup

  1. filtrationfiltered
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe mixture was purified by silica gel chromatography
  8. washeluting with a gradient of 0-100% EtOAc in heptane

Sources & evidence

ORD record
ord-656274f6e6a640d2a3940e03bacbe091
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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