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

HRID 386409Notes

Reaction equation

HRID 386409 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) (820 mg, 2.9 mmol) in dimethylformamide (7 ml) under nitrogen. After 30 minutes tosyl chloride (570 mg, 3 mmol) 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-4ef75f7d56b544ea8cc92646fa0fdf70
Source dataset
uspto-grants-2013_02
Patent number
US08372835B2

Reaction notes

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