Water → HCID 67003430, compound

HRID 2362716Notes

Reaction equation

HRID 2362716 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([Cl: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.O>CN(C)C=O>[Cl:13][C:5]1[C:4]([Cl:3])=[CH:9][N:8]=[C:7]2[N:10]([S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=3)(=[O:22])=[O:21])[CH:11]=[CH:12][C:6]=12

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 467379024,5-Dichloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67003430HCID 67003430, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a cold (0° C.) suspension of sodium hydride (60% dispersion in mineral oil, 0.556 g, 13.9 mmol) in N,N-dimethylformamide (20 mL) was added a solution of the 5-chloro-4-chloro-1H-pyrrolo[2,3-b]pyridine (2 g, 10.69 mmol) in N,N-dimethylformamide (10 mL) slowly over 5 minutes. The reaction was allowed to stir at ambient temperature for 0.5 hours, and was again cooled to 0° C. A solution of para-toluenesulfonyl chloride (2.14 g, 11.23 mmol) in N,N-dimethylformamide (5 mL) was added, and the reaction was stirred at ambient temperature for 1.5 hours. The reaction was poured into 60 mL water cooled in an ice bath. The suspension was filtered. The solid was collected and purified by flash chromatography on a silica gel, eluting with a gradient of 30% to 100% dichloromethane in hexane, to provide the title compound. MS ESI(+) m/z 340.8 [M+H]+.

Workup

  1. temperaturewas again cooled to 0° C
  2. stirringthe reaction was stirred at ambient temperature for 1.5 hours
  3. temperaturecooled in an ice bath
  4. filtrationThe suspension was filtered
  5. customThe solid was collected
  6. custompurified by flash chromatography on a silica gel
  7. washeluting with a gradient of 30% to 100% dichloromethane in hexane

Sources & evidence

ORD record
ord-0664d2416833490b9fefa06d05488941
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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