Potassium Carbonate → HCID 22477296, compound

HRID 1765615Notes

Reaction equation

HRID 1765615 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:33]([S:34]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[C:28]3=[N:29][CH:30]=[CH:31][CH:32]=[C:27]3[CH:26]=2)=[CH:9]1>CN(C)C=O>[CH2:10]([O:2][C:1]([N:29]1[CH2:30][CH2:31][C:32]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([CH3:7])[CH:9]=[C:10]3[C:25]2[N:33]([S:34]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)(=[O:35])=[O:36])[C:28]3=[N:29][CH:30]=[CH:31][CH:32]=[C:27]3[CH:26]=2)=[CH:27][CH2:28]1)=[O:4])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86590753HCID 86590753, compound3×

Product 1

HCID 22477296HCID 22477296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of benzyl 1-[3,6-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl](2H)pyridinecarboxylate (2 g, prepared according to the procedure described by P. Eastwood, Tetrahedron Letters, 2000, 41, pages 3705–3708), dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium[II] (0.25 g,) and potassium carbonate (2.42 g), under nitrogen, was treated with a solution of trifluoro-methanesulfonic acid 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-yl ester [1.6 g, Reference Example 18(a)] in dimethylformamide (76 mL). The mixture was heated at 80° C. for 4 hours (tlc indicated that starting material was still present), then treated with a further quantity of trifluoro-methanesulfonic acid 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-yl ester (0.15 g), then heated at reflux temperature for 4 hours and then left at room temperature overnight. A further quantity of trifluoro-methanesulfonic acid 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-yl ester [0.15 g, Reference Example 18(a)] was added and the mixture was heated at reflux temperature for a further 4 hours then evaporated. The residue was partitioned between ethyl acetate and water, and the aqueous layer was extracted three times with ethyl acetate (50 mL). The combined organic phases were washed with brine, then dried over magnesium sulfate and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1, v/v) to give the title compound as a light brown viscous liquid which was used without further purification.

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureat reflux temperature for 4 hours
  4. temperaturethe mixture was heated
  5. temperatureat reflux temperature for a further 4 hours
  6. customthen evaporated
  7. customThe residue was partitioned between ethyl acetate and water
  8. extractionthe aqueous layer was extracted three times with ethyl acetate (50 mL)
  9. washThe combined organic phases were washed with brine
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1

Sources & evidence

ORD record
ord-13a5cfa744454d0e8288f44e226c6f5f
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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