m-Chloroperbenzoic acid → HCID 49758908, compound

HRID 641894Notes

Reaction equation

HRID 641894 reaction equation
ClC1C=CC=C([C:8]([O:10]O)=[O:9])C=1.[C:12]1([S:18]([N:21]2[C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[C:23](C=O)=[CH:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH:8]([O:10][C:23]1[C:24]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:21]([S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])[CH:22]=1)=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 103566461-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 49758908HCID 49758908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 250 mL 3-necked round bottom flask was placed dichloromethane (30 mL). To the mixture was added mCPBA (m-chloroperbenzoic acid) (2.78 g, 13.69 mmol), while cooling to a temperature of 0° C. This was followed by the addition of a solution of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (3 g, 10.49 mmol) in dichloromethane (100 mL), which was added dropwise with stirring, while cooling to a temperature of 0° C. The resulting solution was allowed to react, with stirring, 2 hours while the temperature was maintained at 0° C. Then the resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 30° C. in a bath of oil. The reaction progress was monitored by LC-MS. The residue was purified by eluting through a column with a 1:10 ethyl acetate/petroleum ether solvent system. This resulted in 2 g (63%) of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl formate as a light yellow solid.

Workup

  1. customInto a 250 mL 3-necked round bottom flask was placed
  2. additionwas added dropwise
  3. temperaturewhile cooling to a temperature of 0° C
  4. customto react
  5. stirringwith stirring, 2 hours while the temperature
  6. temperaturewas maintained at 0° C
  7. customto react
  8. stirringwith stirring, overnight while the temperature
  9. temperaturewas maintained at 30° C. in a bath of oil
  10. customThe residue was purified
  11. washby eluting through a column with a 1:10 ethyl acetate/petroleum ether solvent system
  12. customThis resulted in 2 g (63%) of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl formate as a light yellow solid

Sources & evidence

ORD record
ord-a6a0fae6c8f64b7cbac1fa18c0c15ddf
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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