Dichloromethane → HCID 57891729, compound

HRID 1820883Notes

Reaction equation

HRID 1820883 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+].C[C:23]1[CH:24]=[C:25]2[C:30](=[C:31]([S:33](Cl)(=[O:35])=[O:34])[CH:32]=1)[N:29]=[CH:28][CH:27]=[CH:26]2.[CH2:37](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:33]([C:31]3[CH:32]=[CH:23][CH:24]=[C:25]4[C:30]=3[N:29]=[CH:28][C:27]([CH3:37])=[CH:26]4)(=[O:34])=[O:35])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridineHCID 130081556-Methylquinoline-8-sulfonyl chloride

Product 1

HCID 57891729HCID 57891729, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo-[2,3-b]pyridine, 1, (40 mg, 0.1 mmol) was dissolved in methylene chloride (4 mL). Aqueous potassium hydroxide (50% wt/vol, 300 μL) and tetrabutylammonium hydrogen sulfate (20 mg, 0.007 mmol) were added. The reaction mixture was stirred for 10 minutes at room temperature. Into the reaction was added 6-methyl-quinoline-8-sulfonyl chloride (68 mg, 0.28 mmol), prepared as described (Lubenets, V. I.; Stadnitskaya, N. E.; Novikov, V. P.; Russ. J. Org. Chem.; 36; 2000; 851-853) 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 the resulting solid was washed with acetonitrile to provide 24 (43 mg, 60%). MS(ESI) [M+H+]+=460.1.

Workup

  1. customprepared
  2. stirringthe reaction mixture was stirred for 2 hours at room temperature
  3. concentrationThe reaction mixture was concentrated
  4. washthe residue was washed with brine and ethyl acetate
  5. dry with materialThe organic portion was dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. washthe resulting solid was washed with acetonitrile

Sources & evidence

ORD record
ord-828ab19a48b940b58943c63bf60c7892
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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