Water → 4-chloro-5-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1923705Notes

Reaction equation

HRID 1923705 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([I:10])=[CH:8][N:7]=[C:6]2[NH:11][CH:12]=[CH:13][C:5]=12.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O>[Cl:3][C:4]1[C:9]([I:10])=[CH:8][N:7]=[C:6]2[N:11]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[CH:12]=[CH:13][C:5]=12

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 242292794-Chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 602053064-chloro-5-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (0.960 g, 24.0 mmol, 60% dispersion in mineral oil) at 0° C. was added to 4-chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine (5.57 g, 20.0 mmol) in dimethylformamide (“DMF”; 40 mL) and stirred at 0° C. for 20 minutes. Benzenesulfonyl chloride (2.82 mL, 22.0 mmol) was added, and the reaction was stirred at room temperature for 2 hours. Water (200 mL) was added and stirred for 10 minutes. The solid formed was collected by filtration, washed with ether, and dried to give 4-chloro-5-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (8.20 g, 98% yield).

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. stirringstirred for 10 minutes
  3. customThe solid formed
  4. filtrationwas collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-b02027e075e5487bb3480b99ca939a32
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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