1H-Pyrrolo(2,3-b)pyridine → 3-Chlorobenzoic Acid

HRID 911195Notes

Reaction equation

HRID 911195 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([C:17]([O:19]O)=[O:18])[CH:11]=1>CCOC(C)=O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[NH+:1]1([O-:18])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[CH:11]=1

Participants

6

Reactant 2

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 70297m-Chloroperbenzoic acid

Product 3

HCID 4473-Chlorobenzoic AcidHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 219590977-aza-1H-indole N-oxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

The title compound was prepared according to the procedure described in WO2003082289A1. A solution of 1H-pyrrolo[2,3-b]pyridine (10.0 g, 84.6 mmol) in EtOAc (846 ml, 84.6 mmol) was cooled to 0° C. To the cold solution was added a solution of mCPBA (103 mmol, 23.1 g, 77% pure) in 53 mL of EtOAc over a period of 1.5 h. An additonal 100 mL of EtOAc was added to dilute the reaction. The residual of mCPBA was washed into the reaction mixture by an additional portion of EtOAc (25 mL). A lot of solid precipitated out of the solution. The resulting solution was warmed to rt, and allowed to stir at RT for 3 h. The reaction mixture was cooled to 0° C. and the resulting slurry was filtered to collect the N-oxide as the meta-chlorobenzoic acid salt. The solid was washed with additional EtOAc and dried under vacuum. The product, 1H-pyrrolo[2,3-b]pyridine 1-oxide salt of mCBA was obtained as light yellow solid. 1H NMR in deuterated MeOH indicated predominately the mCBA salt of the N-oxide.

Workup

  1. additionto dilute
  2. customthe reaction
  3. washThe residual of mCPBA was washed into the reaction mixture by an additional portion of EtOAc (25 mL)
  4. customA lot of solid precipitated out of the solution
  5. temperatureThe reaction mixture was cooled to 0° C.
  6. filtrationthe resulting slurry was filtered
  7. customto collect the N-oxide as the meta-chlorobenzoic acid salt
  8. washThe solid was washed with additional EtOAc
  9. customdried under vacuum

Sources & evidence

ORD record
ord-d04ebe2a924d445e849b7f48d773d909
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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