Potassium Hydroxide → 8-[3-(3,4-Dimethoxy-phenyl)-indole-1-sulfonyl]-quinoline

HRID 1820882Notes

Reaction equation

HRID 1820882 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[CH: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.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[CH: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 447206813-(3,4-Dimethoxyphenyl)-1H-indole

Product 1

HCID 578917668-[3-(3,4-Dimethoxy-phenyl)-indole-1-sulfonyl]-quinolineYield 90%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

3-(3,4-Dimethoxy-phenyl)-indole 22 (70 mg, 0.28 mmol) was dissolved in methylene chloride (5.0 mL). Tetra-N-butylammonium bromide (3 mg, 0.01 mmol) and aqueous potassium hydroxide (50% wt/vol, 500 μL) were added. The reaction mixture was stirred for 5 minutes. 8-quinoline-sulfonyl chloride (89.5 mg, 0.39 mmol) was added and the reaction mixture was stirred for 2 hours. The product was extracted with 2 N lithium hydroxide and methylene chloride. The organic portion was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and purified by flash chromatography (ethyl acetate:hexanes 0%-50%). The appropriate fractions were combined and concentrated to provide 21, (76.1 mg, 90%). MS(ESI) [M+H+]+=445.0.

Workup

  1. stirringthe reaction mixture was stirred for 2 hours
  2. extractionThe product was extracted with 2 N lithium hydroxide and methylene chloride
  3. dry with materialThe organic portion was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography (ethyl acetate:hexanes 0%-50%)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-44deb638c5214308be035a0fb33e4a49
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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