Triacetoxyperiodinane → 2-Fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyridine-3-carbaldehyde

HRID 57939Notes

Reaction equation

HRID 57939 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([N:10]2[C:18]3[CH:17]=[C:16]([C:19]4[CH:24]=[N:23][CH:22]=[C:21]([CH3:25])[N:20]=4)[N:15]=[CH:14][C:13]=3[CH:12]=[N:11]2)[N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([N:10]2[C:18]3[CH:17]=[C:16]([C:19]4[CH:24]=[N:23][CH:22]=[C:21]([CH3:25])[N:20]=4)[N:15]=[CH:14][C:13]=3[CH:12]=[N:11]2)[N:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86707123[2-Fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-3-pyridyl]methanol

Product 1

HCID 867071242-Fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyridine-3-carbaldehydeYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [2-fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-3-pyridyl]methanol (0.236 mmol; 79.5 mg) in dichloromethane (10 mL) was added DESS-MARTIN periodinane (0.355 mmol; 155 mg). The mixture as stirred at room temperature for 4 hours. The mixture was concentrated and the residue was purified on silica eluted with 0 to 100% EtOAc in DCM to afford 2-fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyridine-3-carbaldehyde as a pale yellow solid (69.7 mg, 88%).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified on silica
  3. washeluted with 0 to 100% EtOAc in DCM

Sources & evidence

ORD record
ord-34d27d8121b146bb819dc9b6d92940ba
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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