Triacetoxyperiodinane → HCID 68637014, compound

HRID 2234129Notes

Reaction equation

HRID 2234129 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([CH:39]([OH:41])[CH3:40])[CH:37]=2)[CH:32]=[C:31]1[C:42]1[CH:47]=[C:46]([C:48]2[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=2)[N:45]=[N:44][C:43]=1[O:54][CH3:55])=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl>[C:23]([O:27][C:28]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:39](=[O:41])[CH3:40])[CH:37]=2)[CH:32]=[C:31]1[C:42]1[CH:47]=[C:46]([C:48]2[CH:49]=[CH:50][N:51]=[CH:52][CH:53]=2)[N:45]=[N:44][C:43]=1[O:54][CH3:55])=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68638205HCID 68638205, compound

Product 1

HCID 68637014HCID 68637014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg Dess-Martin periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) is added to a solution of 210 mg 6-(1-hydroxy-ethyl)-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butylester (145a) in 4 ml dichloromethane and the mixture stirred for 2.5 hours at room temperature. Than the solution is extracted with a 5% Na2SO3 solution and water, dried using a silicagel cartridge and the solvent removed in vacuo. The crude product is purified by chromatography on silica gel (heptane/ethylacetate)

Workup

  1. extractionThan the solution is extracted with a 5% Na2SO3 solution and water
  2. customdried
  3. customthe solvent removed in vacuo
  4. customThe crude product is purified by chromatography on silica gel (heptane/ethylacetate)

Sources & evidence

ORD record
ord-1b72875ca2584b268f0a87b32dd27899
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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