Potassium Hydroxide → HCID 57891763, compound

HRID 1820879Notes

Reaction equation

HRID 1820879 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[K+].[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[S:32](Cl)(=[O:34])=[O:33])[CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([S:32]([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:31]=3[N:22]=[CH:23][CH:24]=[CH:25]4)(=[O:33])=[O:34])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 292208-Quinolinesulfonyl chlorideHCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57891763HCID 57891763, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo-[2,3-b]pyridine, 1, (50 mg, 0.20 mmol) was dissolved in methylene chloride (4 mL). Aqueous potassium hydroxide (50% wt/vol, 300 μL) and tetrabutylammonium hydrogen sulfate (2 mg, 0.007 mmol) were added. The reaction mixture was stirred for 10 minutes at room temperature. Into the reaction was added 8-quinoline-sulfonyl chloride (48 mg, 0.21 mmol) and the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated and the residue was washed with brine and ethyl acetate. The organic portion was dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by preparative TLC (75% ethyl acetate:hexanes). The product was eluted from the silica with ethyl acetate and filtration. The filtrate was concentrated to provide 7 (14 mg, 16%). MS(ESI) [M+H+]+=445.9.

Workup

  1. stirringthe reaction mixture was stirred for 2 hours at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. washthe residue was washed with brine and ethyl acetate
  4. dry with materialThe organic portion was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by preparative TLC (75% ethyl acetate:hexanes)
  8. washThe product was eluted from the silica with ethyl acetate and filtration
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dff8167922034269b244c65da70dedbc
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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