4-Toluenesulfonyl chloride → HCID 118274348, compound

HRID 522225Notes

Reaction equation

HRID 522225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([CH:11]=[O:12])[C:3]=12.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[CH:9]=[C:10]([CH:11]=[O:12])[C:3]=12

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 247295674-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 118274348HCID 118274348, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of Example 127A (1 g, 5.54 mmol) in toluene (10 mL) was added p-toluenesulfonyl chloride (1.584 g, 8.31 mmol) and tetrabutylammonium hydrogensulfate (0.188 g, 0.554 mmol). The mixture was cooled to 0° C., and a solution of sodium hydroxide (0.554 g, 13.84 mmol) in water (2 mL) was added. The mixture was stirred at room temperature overnight, and partitioned between ethyl acetate and water. The organic phase was washed with water and concentrated. The residue was triturated with 10% ethyl acetate in heptane and filtered to provide the title compound. MS (ESI+) m/z 335 (M+H)+.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with water
  3. concentrationconcentrated
  4. customThe residue was triturated with 10% ethyl acetate in heptane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-acc782e2436f43fc8fba834bf58d57d4
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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