m-Chloroperbenzoic acid → HCID 59605785, compound

HRID 1945579Notes

Reaction equation

HRID 1945579 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>O1CCOCC1>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N+:15]([O-:27])=[CH:14][C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 110106571-(Phenylsulfonyl)-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 59605785HCID 59605785, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 100 mL round-bottomed flask was charged with a solution of 1-benzenesulfonyl-1H-pyrrolo[3,2-c]pyridine (0.6 g, 2.3 mmol) in dioxane (20 mL). To the resultant solution was added mCPBA (0.6 g, 3.45 mmol) and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated in vacuo then the residue was dissolved in DCM (50 mL), and washed successively with aqueous sodium sulfite solution, aqueous sodium bicarbonate solution and brine. The organic layer was isolated then dried (Na2SO4) and concentrated in vacuo to give the title compound as a white solid (0.6 g, 95%). 1H NMR (DMSO, 300 MHz): δ 8.61 (dd, J=1.8, 0.7 Hz, 1 H); 8.13 (dd, J=7.2, 1.8 Hz, 1 H); 8.09-8.04 (m, 2 H); 8.01 (d, J=3.7 Hz, 1 H); 7.92 (d, J=7.2 Hz, 1 H); 7.80-7.73 (m, 1 H); 7.69-7.61 (m, 2 H); 6.83 (dd, J=3.7, 0.8 Hz, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in DCM (50 mL)
  3. washwashed successively with aqueous sodium sulfite solution, aqueous sodium bicarbonate solution and brine
  4. customThe organic layer was isolated
  5. dry with materialthen dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-632525a327bc481fb3bda5f8ad8bab25
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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