Sodium Iodide → HCID 67147845, compound

HRID 490526Notes

Reaction equation

HRID 490526 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]2[N:24]([S:41]([C:44]3[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=3)(=[O:43])=[O:42])[C:25]([C:27]3[C:35]4[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36][CH3:37])[CH:34]=4)[N:29]([CH3:40])[CH:28]=3)=[CH:26][C:19]=12>C(#N)C.O.C(OCC)(=O)C>[CH3:37][O:36][C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][C:32]=1[O:38][CH3:39])[N:29]([CH3:40])[CH:28]=[C:27]2[C:25]1[N:24]([S:41]([C:44]2[CH:45]=[CH:46][C:47]([CH3:50])=[CH:48][CH:49]=2)(=[O:43])=[O:42])[C:20]2=[N:21][CH:22]=[CH:23][C:18]([CH2:17][N:1]3[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]3)=[C:19]2[CH:26]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 67147535HCID 67147535, compound

Product 1

HCID 67147845HCID 67147845, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

0.027 g of piperid-4-ol, 0.075 g of potassium carbonate and 0.016 g of sodium iodide are added to a solution of 0.055 g of 4-chloromethyl-2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in 3 cm3 of acetonitrile, at a temperature in the region of 20° C. The reaction medium is heated at 80° C. for one hour. After cooling, the reaction medium is filtered through a sinter funnel and the filtrate is concentrated under reduced pressure. The residue obtained is taken up in 3 cm3 of water and 4 cm3 of ethyl acetate. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.049 g of [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]piperid-4-ol is obtained, the characteristics of which are as follows:

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction medium is filtered through a sinter funnel
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. customAfter separation of the phases
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14ae3da87e684d99abcff297072eb293
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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