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

HRID 509926Notes

Reaction equation

HRID 509926 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[C:14]1([S:20]([N:8]2[C:5]3=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:10]([I:11])=[CH:9]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 242292205-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292391-Benzenesulfonyl-5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridineYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (2, 5.00 g, 18.0 mmol) in 80.0 mL of N,N-dimethylformamide, sodium hydride (1.1 g, 60% in mineral oil, 27.0 mmol) was added slowly. A solution of benzenesulfonyl chloride (11, 2.40 mL, 18.8 mmol) in 10.0 mL of N,N-dimethylformamide was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 15 hours, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting solid was washed with 5% ethyl acetate in hexane, isolated by filtration, and dried to provide the desired compound (12, 5.9 g). 1H NMR was consistent with the compound structure. 1-Benzenesulfonyl-3-iodo-5-methyl-1H-pyrrolo[2,3-b]pyridine 13

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. washThe resulting solid was washed with 5% ethyl acetate in hexane
  7. customisolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-6a9d1b3fd78246d69aca0f5525b3c236
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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