Potassium Carbonate → {5-methoxy-1-methoxycarbonylmethyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-yloxy}acetic acid

HRID 490466Notes

Reaction equation

HRID 490466 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[NH:8][CH:7]=[C:6]2[C:13]1[N:21]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH3:43])=[O:41].C1CCCCC1.[C:50]([O:53]CC)(=[O:52])[CH3:51]>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH2:51][C:50]([OH:53])=[O:52])[N:8]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:7]=[C:6]2[C:13]1[N:21]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 21867204Cyclohexane ethylacetateHCID 671475805-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol

Product 1

HCID 67147571{5-methoxy-1-methoxycarbonylmethyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-yloxy}acetic acidYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol (0.043 g; 100 μmol), in solution in dimethylformamide (10 ml), is placed in a 1.3×10 cm hemolysis tube, then potassium carbonate (0.027 g; 200 μmol) is added and the mixture is agitated at ambient temperature for 5 minutes. Methyl bromoacetate (0.028 ml; 300 μmol) is added and the mixture is then heated at 50° C. for 4 hours, the TLC control (eluent: 50/50 v/v cyclohexane/ethyl acetate) showing that the reaction has come to an end. The reaction mixture is run into 5 ml of distilled water and the reaction mixture is then extracted with ethyl acetate (15 ml). The combined extracts are washed with water (20 ml), dried over magnesium sulfate, filtered, and evaporated to give a crude compound which is purified by chromatography on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (60/40 v/v). The fractions containing the expected compound are combined and evaporated to give the methyl ester of {5-methoxy-1-methoxycarbonylmethyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-yloxy}acetic acid (0.056 g; 97%), the characteristics of which are as follows:

Workup

  1. temperaturethe mixture is then heated at 50° C. for 4 hours
  2. extractionthe reaction mixture is then extracted with ethyl acetate (15 ml)
  3. washThe combined extracts are washed with water (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude compound which
  8. customis purified by chromatography on silica gel, elution
  9. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (60/40 v/v)
  10. additionThe fractions containing the expected compound
  11. customevaporated

Sources & evidence

ORD record
ord-a46bb1ab27714338aa7aeceb9b18d94c
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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