4-Toluenesulfonyl chloride → HCID 86689825, compound

HRID 2409014Notes

Reaction equation

HRID 2409014 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]>C1COCC1>[S:14]([N:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 228320511H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 86689825HCID 86689825, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

step2: To a solution of 1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (500 mg, 3.42 mmol) in THF (50 mL) at 0° C. was added NaH (205 mg, 60% in oil, 5.13 mmol) with vigorous stirring. After 30 min, TsCl (845 mg, 4.45 mmol) was added. The reaction mixture was stirred at RT for 18 h, and then the solvent was removed in vacuo. The residue was partitioned between DCM (300 mL) and water (100 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated to afford 580 mg (56%) of 1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde as yellow solid. MS (ESI) m/z: 301.2 [M+1]+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between DCM (300 mL) and water (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fa848acf974f4bc688c4abc6294003d9
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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