Triacetoxyperiodinane → HCID 117987725, compound

HRID 2206064Notes

Reaction equation

HRID 2206064 reaction equation
[Br:1][C:2]1[C:3]([CH:11]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[OH:12])=[C:4]([F:10])[C:5]([O:8][CH3:9])=[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[C:3]([C:11]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[C:4]([F:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 117987829HCID 117987829, compound

Product 1

HCID 117987725HCID 117987725, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (5-bromo-3-fluoro-2-methoxypyridin-4-yl)(cyclopentyl)methanol (430 mg) in acetonitrile (10 mL) was added Dess-Martin reagent (720 mg) at room temperature, and the mixture was stirred for 3 hr, and the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane) to give the title compound (440 mg).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-026453513ee54243b5956ef8ec5928dc
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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