4-Toluenesulfonyl chloride → 2-Chloro-7-iodo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

HRID 1713005Notes

Reaction equation

HRID 1713005 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.[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]>CN(C)C=O>[Cl:3][C:4]1[N:5]=[C:6]2[C:12]([I:13])=[CH:11][N:10]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 536276902-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 594635242-Chloro-7-iodo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (140 mg, 3.5 mmol) was added to an ice-cold solution of 2-chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine (5) (820mg, 2.9mmol) in dimethylformamide (7 ml) under nitrogen. After 30 minutes tosyl chloride (570mg, 3mmol) was added to the reaction mixture and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was then quenched with water (15 ml). An off white solid was filtered off and dried in vacuo (950 mg, 75%). MS(ES+) 434.

Workup

  1. customThe reaction mixture was then quenched with water (15 ml)
  2. filtrationAn off white solid was filtered off
  3. customdried in vacuo (950 mg, 75%)

Sources & evidence

ORD record
ord-407de755704d4c7d982022221df28f07
Source dataset
uspto-grants-2010_09
Patent number
US07795259B2

Reaction notes

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