4-Toluenesulfonyl chloride → HCID 86689845, compound

HRID 2409030Notes

Reaction equation

HRID 2409030 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[NH:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 260764006-Chloro-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 86689845HCID 86689845, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-1H-pyrrolo[3,2-b]pyridine (5.0 g, 32.8 mmol) in THF (150 mL) in an ice bath was added NaH (1.57 g, 60% in mineral oil, 39.3 mmol). After stirring in an ice bath for 30 min, 4-toluenesulfonyl chloride (6.87 g, 36.1 mmol) was added. The mixture was stirred at RT overnight. The reaction mixture was quenched with water (50 mL) at 0° C. and extracted with EtOAc (300 mL). The extract was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc gradient (8:1 to 2:1) to afford 6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridine as a yellow solid (8.5 g, 84%). MS (ESI): m/z=307.0 [M+1]+.

Workup

  1. stirringThe mixture was stirred at RT overnight
  2. customThe reaction mixture was quenched with water (50 mL) at 0° C.
  3. extractionextracted with EtOAc (300 mL)
  4. dry with materialThe extract was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with petroleum ether/EtOAc gradient (8:1 to 2:1)

Sources & evidence

ORD record
ord-f9fa7b934b134d3b887d7a28512aaac4
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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