Triacetoxyperiodinane → 1-(5-Bromopyridin-3-yl)cyclopropane-1-carbaldehyde

HRID 1521613Notes

Reaction equation

HRID 1521613 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:11][OH:12])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:11]=[O:12])[CH2:9][CH2:10]2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 77230757HCID 77230757, compound

Product 1

HCID 891558951-(5-Bromopyridin-3-yl)cyclopropane-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the title compound from Example 73 Step A (114 mg, 0.500 mmol) in acetonitrile (2.5 mL) was added Dess-Martin Periodinane (254 mg, 0.600 mmol). The reaction stirred at room temperature until complete. It was then concentrated under reduced pressure, diluted with 2% methanol in dichloromethane, and passed through a syringe filter. Purification by flash chromatography on silica gel (20-100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 227.86 [M+2+H]+.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. additiondiluted with 2% methanol in dichloromethane
  3. custompassed through a syringe
  4. filtrationfilter
  5. customPurification by flash chromatography on silica gel (20-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-033586360edb4334b03161ae201d05fe
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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