Sodium Iodide → HCID 67147680, compound

HRID 490443Notes

Reaction equation

HRID 490443 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH2:24][CH2:25]Cl)[CH:12]=3)=[CH:10][C:3]=12.[I-:37].[Na+]>CC(=O)CC>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH2:24][CH2:25][I:37])[CH:12]=3)=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 671474024-chloro-2-[1-(2-chloroethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67147680HCID 67147680, compoundYield 110.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 0.760 g of 4-chloro-2-[1-(2-chloroethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 0.315 g of sodium iodide in 70 ml of 2-butanone is brought to reflux for approximately 24 hours. The reaction mixture is evaporated to dryness under reduced pressure (13 kPa), taken up with 50 ml of water, and extracted with three times 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). 0.98 g of 4-chloro-2-[1-(2-iodoethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is obtained in the form of a yellow oil, the characteristics of which are as follows:

Workup

  1. temperatureto reflux for approximately 24 hours
  2. customThe reaction mixture is evaporated to dryness under reduced pressure (13 kPa)
  3. extractionextracted with three times 50 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-64bcf233dd844d9e883d180549f4e754
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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