Water → HCID 57731423, compound

HRID 2234710Notes

Reaction equation

HRID 2234710 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:22]=[CH:21][NH:20][N:19]=3)[CH:16]=2)[NH:11][CH:10]=1.[H-].[Na+].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.[OH2:36]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:22]=[CH:21][N:20]([S:31]([C:28]4[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=4)(=[O:33])=[O:32])[N:19]=3)[CH:16]=2)[N:11]([S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:32])=[O:36])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178489320HCID 178489320, compound

Product 1

HCID 57731423HCID 57731423, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxy-phenyl)-5-(1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine (500 mg, 1.12 mmol) was dissolved in tetrahydrofuran (10 mL) and cooled in an ice bath. Sodium hydride (60% oil dispersion, 103 mg, 2.58 mmol) was added, followed by p-toluene-sulfonylchloride (TsCl) (361 mg, 1.89 mmol). After stirring 19 h, deionized water was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate (1×) and brine (1×) and dried over sodium sulfate. The material was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-5-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (458 mg, 68.4%). MS: m/z 599 (M+H+).

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with saturated sodium bicarbonate (1×) and brine (1×)
  5. dry with materialdried over sodium sulfate
  6. customThe material was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9e935f6ee5d6498c8b3c956bcc52ef48
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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