Sodium Hydroxide → 8-((3-Bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)sulfonyl)quinoline

HRID 1820886Notes

Reaction equation

HRID 1820886 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[OH-].[Na+].[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[S:23](Cl)(=[O:25])=[O:24])[CH:16]=[CH:15][CH:14]=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].ClCCl>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:23]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:22]=2[N:13]=[CH:14][CH:15]=[CH:16]3)(=[O:24])=[O:25])[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 292208-Quinolinesulfonyl chlorideHCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 578916868-((3-Bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)sulfonyl)quinolineYield 74%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Into a round bottom flask was added 3-bromo-7-azaindole (3, 1.18 g, 5.99 mmol) and tetra-N-butylammonium bromide (193 mg, 0.600 mmol), and 5.0 M sodium hydroxide (15.4 mL). 8-Quinoline-sulfonyl chloride (1.64 g, 7.19 mmol) in dichloromethane (5.9 mL) was added dropwise at room temperature. After a few hours, all starting materials were gone. After 30 mL of dichlormethane was added, two layers were separated. The aqueous layer was washed with dichloromethane. The combined organic layers were washed with 1 M sodium bicarbonate, water, and brine and dried over anhydrous sodium sulfate. The crude material was concentrated under reduced pressure and was purified by column chromatography (55-80% ethyl acetate in hexane) to yield the desired product as a light yellow colored solid (44, 1.72 g, 4.43 mmol). MS(ESI) [M+H+]+=389.4.

Workup

  1. waitAfter a few hours
  2. customtwo layers were separated
  3. washThe aqueous layer was washed with dichloromethane
  4. washThe combined organic layers were washed with 1 M sodium bicarbonate, water, and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe crude material was concentrated under reduced pressure
  7. customwas purified by column chromatography (55-80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0b3e465459264aa1bd63f7e87f825df2
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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