Triacetoxyperiodinane → HCID 86717916, compound

HRID 2275832Notes

Reaction equation

HRID 2275832 reaction equation
C(OI1(OC(=O)C)(OC(=O)C)C2C=CC=CC=2C(=O)O1)(=O)C.[F:23][C:24]1[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:25]=1[CH2:26][O:27][C:28]1[C:29]2[N:30]([C:34]([C:38]([NH:40][CH2:41][CH2:42][OH:43])=[O:39])=[C:35]([CH3:37])[N:36]=2)[CH:31]=[CH:32][CH:33]=1>ClCCl.C(OCC)(=O)C>[F:23][C:24]1[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:25]=1[CH2:26][O:27][C:28]1[C:29]2[N:30]([C:34]([C:38]([NH:40][CH2:41][CH:42]=[O:43])=[O:39])=[C:35]([CH3:37])[N:36]=2)[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86717917HCID 86717917, compound

Product 1

HCID 86717916HCID 86717916, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 1.65 g 1,1,1-triacetoxy-1lambda5,2-benziodoxol-3(1H)-one (Dess-Martin periodinane, 3.9 mmol, 1.5 equivalents) were initially charged in 20 ml of dichloromethane. At −25° C., a solution of 1 g of 8-[(2,6-difluorobenzyl)oxy]-N-(2-hydroxyethyl)-2-methylimidazo-[1,2-a]pyridine-3-carboxamide (Example 175A, 2.6 mmol, 1 equivalent) in 32 ml of dichloromethane was slowly added dropwise. The reaction mixture was stirred overnight, warming to RT. The reaction solution was then diluted with about 160 ml of ethyl acetate and washed three times with 1 N aqueous sodium hydroxide solution. The organic phase was washed with saturated aqueous sodium chloride solution until neutral, dried over sodium sulphate, filtered and concentrated. This gave 879 mg (47% of theory; purity about 50%) of the title compound which was reacted further without purification.

Workup

  1. washwashed three times with 1 N aqueous sodium hydroxide solution
  2. washThe organic phase was washed with saturated aqueous sodium chloride solution until neutral,
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis gave 879 mg (47% of theory; purity about 50%) of the title compound which was reacted further without purification

Sources & evidence

ORD record
ord-474d0d8430254d4793936bff72a2d3f1
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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