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1,2-Dichloroethane → 4-chloro-2-[1-(2-chloroethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2426840
Notes
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Reaction equation

HRID 2426840 reaction equation
[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:17]([C:19]3[C:27]4[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=4)[NH:21][CH:20]=3)=[CH:18][C:11]=12.[Cl:42][CH2:43][CH2:44]Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:17]([C:19]3[C:27]4[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=4)[N:21]([CH2:44][CH2:43][Cl:42])[CH:20]=3)=[CH:18][C:11]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 671474254-chloro-2-(5,6-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

0.79 g of potassium hydroxide and 0.61 g of potassium carbonate are added to a solution of 1 g of 4-chloro-2-(5,6-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 0.013 g of tetrabutylammonium bromide in 25 ml of 1,2-dichloroethane. The suspension obtained is brought to around 50° C. for approximately 5 hours. After returning to a temperature in the region of 20° C. and agitating at this temperature for approximately 16 hours, the reaction mixture is filtered through celite; the insoluble material is washed with three times 10 ml of dichloromethane. The filtrate is washed with three times 50 ml of water, dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure. The residue is purified by flash chromatography on a silica column [eluent: cyclohexane/ethyl acetate (75/25 by volume)]. 0.62 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 is obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. customThe suspension obtained
  2. customAfter returning to a temperature in the region of 20° C.
  3. filtrationthe reaction mixture is filtered through celite
  4. washthe insoluble material is washed with three times 10 ml of dichloromethane
  5. washThe filtrate is washed with three times 50 ml of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue is purified by flash chromatography on a silica column [eluent: cyclohexane/ethyl acetate (75/25 by volume)]

Sources & evidence

ORD record
ord-a5e103863e2a4be392e771ad46c0c9ea
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968566B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes