Dichloromethane → 8-[4-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline

HRID 1820901Notes

Reaction equation

HRID 1820901 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[NH:17][CH:18]=[CH:19][C:12]=23)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].[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-].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[N:17]([S:32]([C:30]4[CH:29]=[CH:28][CH:27]=[C:26]5[C:31]=4[N:22]=[CH:23][CH:24]=[CH:25]5)(=[O:33])=[O:34])[CH:18]=[CH:19][C:12]=23)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 292208-Quinolinesulfonyl chlorideHCID 119990244-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 578917388-[4-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Into a Round bottom flask was added 4-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (0.222 g, 0.000873 mol), 50 and Tetra-N-butylammonium bromide (0.0282 g, 0.0000874 mol), and 5.000 M of Sodium hydroxide in Water (2.25 mL). 8-quinoline-sulfonyl chloride (0.238 g, 0.00105 mol) dissolved in Methylene chloride (0.616 mL, 0.00960 mol) was added dropwise at 0 Celsius. The reaction was stirred at ambient temperature for 3 h and the reaction mixture was diliuted with an addional 25 mL of methylene chloride. The organic layer was washed with 1 M sodium bicarbonate (aq.) (30 ml×2) and then with brine. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to yield the titled compound as a white solid. MS(ESI) [M+H+]+=446.20.

Workup

  1. additionwas added dropwise at 0 Celsius
  2. washThe organic layer was washed with 1 M sodium bicarbonate (aq.) (30 ml×2)
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8a51a24037a14a77b8424424956fe693
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

Loading…