Water → 1-Benzenesulfonyl-5-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 217596Notes

Reaction equation

HRID 217596 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[Na+].O.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O1CCCC1>[C:14]1([S:20]([N:8]2[C:5]3=[N:6][CH:7]=[C:2]([I:1])[CH:3]=[C:4]3[CH:10]=[CH:9]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 242292145-Iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 509894651-Benzenesulfonyl-5-iodo-1H-pyrrolo[2,3-b]pyridineYield 85.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-Iodo-1H-pyrrolo[2,3-b]pyridine (24, 0.521 g, 2.13 mmol), tetra-N-butylammonium bromide (0.0689 g, 0.214 mmol), and 5.00 M sodium hydroxide in water (5.50 mL, 0.0275 mol) were combined in a round bottom flask. Benzenesulfonyl chloride (28, 0.327 mL, 2.56 mmol) in 5.0 mL of tetrahydrofuran was added dropwise at room temperature. The reaction was stirred at room temperature overnight and the two layers were separated. The aqueous layer was washed with ethyl acetate and the combined organic layers were washed with 1M aqueous sodium bicarbonate followed by water. The organic layer was washed with brine and dried over anhydrous sodium sulfate, then filtered and the filtrate concentrated. The crude material was purified by silica gel flash chromatography eluting with ethyl acetate and dichloromethane. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (29, 0.702 g).

Workup

  1. customthe two layers were separated
  2. washThe aqueous layer was washed with ethyl acetate
  3. washthe combined organic layers were washed with 1M aqueous sodium bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated
  8. customThe crude material was purified by silica gel flash chromatography
  9. washeluting with ethyl acetate and dichloromethane
  10. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-e39f1fd2e13e4d8da6f1ea23de056630
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

Loading…