m-Chloroperbenzoic acid → HCID 67155645, compound

HRID 2196705Notes

Reaction equation

HRID 2196705 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13](C=O)=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13](=[O:30])[CH2:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 454802961-Tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 67155645HCID 67155645, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (5 g, 16.65 mmol) was dissolved in DCM (165 mL) and chilled to 0° C. m-Chloroperbenzoic acid (“m-CPBA”; 4.85 g, 21.64 mmol, 77% by weight) was added, and the mixture was allowed to gradually warm to room temperature over a 16 hour period. The mixture was then washed with 10% aqueous sodium sulfite solution, dried over sodium sulfate and concentrated. Flash 65 Biotage (5% ethyl acetate/DCM) afforded 1-tosyl-1H-pyrrolo[2,3-b]pyridin-3 (2H)-one (441 mg, 9%). 1H NMR (400 MHz, CDCl3) δ 8.61-8.66 (m, 1H), 8.00-8.05 (m, 2H), 7.92-7.97 (m, 1H), 7.29-7.34 (m, 2H), 7.06-7.12 (m, 1H), 4.38 (s, 2H), 2.41 (s, 3H).

Workup

  1. additionwas added
  2. washThe mixture was then washed with 10% aqueous sodium sulfite solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fb68cda7b76245cf8f0f529499b3fbee
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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