Benzenesulfonyl chloride → HCID 87182332, compound

HRID 390109Notes

Reaction equation

HRID 390109 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]2[C:12]([I:13])=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[Cl:3][C:4]1[N:5]=[C:6]2[C:12]([I:13])=[CH:11][N:10]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 536276902-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 87182332HCID 87182332, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in mineral oil, 404 mg, 10.09 mmol) was added to an ice-cold solution of EXAMPLE 33A (2.35 g, 8.41 mmol) in anhydrous DMF (20 mL) under nitrogen. The reaction mixture was stirred at 0° C. for 30 minutes and benzenesulfonyl chloride (1.19 mL, 9.25 mmol) was then added. The ice-bath was removed and the mixture was stirred at room temperature overnight. This reaction was quenched with the addition of 50 mL of water. An off white solid material was collected by filtration, washed with water and hexane, and dried to give 3.38 g of the title product. Yield: 96%. MS (DCI+) m/z 280 (M+H)+.

Workup

  1. customThe ice-bath was removed
  2. stirringthe mixture was stirred at room temperature overnight
  3. customThis reaction was quenched with the addition of 50 mL of water
  4. filtrationAn off white solid material was collected by filtration
  5. washwashed with water and hexane
  6. customdried

Sources & evidence

ORD record
ord-16fa32c4ddd24861b6fbc9090946e6a9
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Reaction notes

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