4-Nitrobenzenesulfonyl chloride → HCID 66691816, compound

HRID 520602Notes

Reaction equation

HRID 520602 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[H][H].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C=O)C.O>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[N:6]([S:24]([C:21]2[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:23][CH:22]=2)(=[O:25])=[O:26])[CH:5]=1

Participants

7

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 124108563-Bromo-1H-pyrrolo[2,3-c]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 66691816HCID 66691816, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in mineral oil) (217 mg) was added to a stirred solution of 3-bromo-1H-pyrrolo[2,3-c]pyridine (535 mg) in DMF (5 ml) that had been cooled in an ice bath to 0° C. and placed under nitrogen. The mixture was stirred for 30 min, until hydrogen evolution ceased, and then 4-nitrobenzenesulfonyl chloride (662 mg) was added. The mixture was stirred at 0° C. for 1 hour. The mixture was then warmed to RT and stirred for a further 30 min. The solution was poured into stirring water (10 ml) and rapidly stirred for 15 min. The resulting brown solid was collected by filtration, washed with water and dried in a vacuum oven at 50° C. to give a yellow solid. This crude material was purified by FlashMaster II. The residue was dissolved in DCM:methanol (1:1) and pre adsorbed onto silica. This was added to the top of a 20 g silica SPE cartridge that was subsequently eluted with 0-50% ethyl acetate:cyclohyexane over 40 min. The product-containing fractions were combined and the solvent removed in vacuo to give the title compound, 233 mg as a white solid.

Workup

  1. temperatureThe mixture was then warmed to RT
  2. stirringstirred for a further 30 min
  3. additionThe solution was poured
  4. stirringrapidly stirred for 15 min
  5. filtrationThe resulting brown solid was collected by filtration
  6. washwashed with water
  7. customdried in a vacuum oven at 50° C.
  8. customto give a yellow solid
  9. customThis crude material was purified by FlashMaster II
  10. dissolutionThe residue was dissolved in DCM:methanol (1:1)
  11. additionThis was added to the top of a 20 g silica SPE cartridge that
  12. washwas subsequently eluted with 0-50% ethyl acetate
  13. waitcyclohyexane over 40 min
  14. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8d50d9b84cb74f38844aaee2c5898725
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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