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

HRID 509928Notes

Reaction equation

HRID 509928 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[C:15]1([S:21]([N:4]2[C:5]3=[N:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[C:10]3[C:2]([I:1])=[CH:3]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 242292443-Iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 591287071-(Benzenesulfonyl)-3-iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridineYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridine (15, 4.30 g, 15.7 mmol) in 53.6 mL of N,N-dimethylformamide under nitrogen, sodium hydride (0.690 g, 60% in mineral oil, 17.2 mmol) was added. After 10 minutes, benzenesulfonyl chloride (11, 2.20 mL, 17.2 mmol) was added and the reaction was cooled in a water bath. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate purified by silica gel column chromatography, eluting with 30-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (16, 4.60 g).

Workup

  1. temperaturethe reaction was cooled in a water bath
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate purified by silica gel column chromatography
  6. washeluting with 30-100% ethyl acetate in hexane
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5d4e50848f19428783ee250d56b8a1cd
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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