Water → 1-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

HRID 69247

Reaction equation

HRID 69247 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[O:11])=[CH:2]1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].O>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18]([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]([CH:10]=[O:11])=[CH:2]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 103566461-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde (200 mg, 1.368 mmol) was dissolved in DCM (8 mL). Then tetra-n-butylammonium hydrogen sulfate (48.4 mg, 0.137 mmol), benzensulfonyl chloride (0.176 mL, 1.37 mmol) and NaOH 50% (0.263 mL, 3.3 mmol) were added. The RM was stirred at rt for 1 h. Water was added and it was extracted with DCM twice. The combined organic layers was washed with brine and dried over Na2SO4, filtered and evaporated to afford the title compound as a light yellow solid (tR 2.0 min (conditions 1), MH+=287).

Workup

  1. extractionit was extracted with DCM twice
  2. washThe combined organic layers was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-920a061c2d4f423bb73537e9753053e2
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Linked notes

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