Pyridine → HCID 86718207, compound

HRID 1844157Notes

Reaction equation

HRID 1844157 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=[O:3].N1C=CC=CC=1.[F:29][C:30]1[CH:57]=[CH:56][CH:55]=[C:54]([F:58])[C:31]=1[CH2:32][O:33][C:34]1[C:35]2[N:36]([C:40]([C:44]([NH:46][C@H:47]([CH2:50][CH2:51][CH2:52][CH3:53])[CH2:48]O)=[O:45])=[C:41]([CH3:43])[N:42]=2)[CH:37]=[CH:38][CH:39]=1.[OH-].[Na+]>ClCCl>[F:29][C:30]1[CH:57]=[CH:56][CH:55]=[C:54]([F:58])[C:31]=1[CH2:32][O:33][C:34]1[C:35]2[N:36]([C:40]([C:44]([NH:46][C@@H:47]([CH2:50][CH2:51][CH2:52][CH:53]=[O:3])[CH3:48])=[O:45])=[C:41]([CH3:43])[N:42]=2)[CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 74222718HCID 74222718, compound

Product 1

HCID 86718207HCID 86718207, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

655 mg of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane; 97%, Aldrich; 1.5 mmol) were initially charged in 10 ml of anhydrous dichloromethane and cooled to about −30° C. 83 μl (1.03 mmol) of pyridine and 430 mg 8-[(2,6-difluorobenzyl)oxy]-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide (1.03 mmol) in 20 ml of dichloromethane were added successively to this suspension. The reaction solution was warmed to room temperature and stirred for a further 4 h. With ice cooling, 1N aqueous sodium hydroxide solution was then added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered off and concentrated. The residue obtained was used without further purification for subsequent reactions.

Workup

  1. temperatureThe reaction solution was warmed to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered off
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas used without further purification for subsequent reactions

Sources & evidence

ORD record
ord-a3bb470089724a879a3d34f28855c4fd
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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