4-Toluenesulfonyl chloride → HCID 67003872, compound

HRID 2362618Notes

Reaction equation

HRID 2362618 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([I:13])=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN(C)C=O>[Cl:3][C:4]1[C:5]([I:13])=[C:6]2[CH:12]=[CH:11][N:10]([S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=3)(=[O:22])=[O:21])[C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 260764205-Chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67003872HCID 67003872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To an ambient suspension of sodium hydride (0.560 g, 23.34 mmol) in N,N-dimethylformamide (40 mL) was added a solution of 5-chloro-4-iodo-1H-pyrrolo[2,3-b]pyridine (5.0 g, 17.95 mmol) (Example 1E) in N,N-dimethylformamide (10 mL) slowly. The reaction was stirred for 0.5 hours, and a solution of para-toluenesulfonyl chloride (3.59 g, 18.85 mmol) in N,N-dimethylformamide (8 mL) was added. The reaction was stirred for 1 hour and was then quenched by pipetting the reaction portionwise into water (50 mL) with vigorous stirring. The solid was filtered and air-dried to give the title compound as a solid. MS ESI(+) m/z 433 [M+H]+.

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. customwas then quenched
  3. customthe reaction portionwise into water (50 mL) with vigorous stirring
  4. filtrationThe solid was filtered
  5. customair-dried

Sources & evidence

ORD record
ord-9b64d037002345348ab7972549c303a2
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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