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

HRID 1013638Notes

Reaction equation

HRID 1013638 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 a procedure described in WO2003082289A1. A solution of 1H-pyrrolo[2,3-b]pyridine (10.0 g, 84.6 mmol) in ethyl acetate (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. Halfway into the reaction, 100 mL of EtOAc was added to the reaction to ease stirring of the thick mixture. The residual mCPBA was washed into the reaction mixture by an additional portion of EtOAc (25 mL). Solid precipitated out of the solution, and the resulting mixture was warmed to rt, and allowed to stir at this temp until the starting azaindole had been consumed as judged by RPLC. After 3 h at rt, the reaction was completed. The reaction mixture was cooled back to 0° C. 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.

Workup

  1. additionwas added to the reaction
  2. washThe residual mCPBA was washed into the reaction mixture by an additional portion of EtOAc (25 mL)
  3. customSolid precipitated out of the solution
  4. stirringto stir at this temp until the starting azaindole
  5. customhad been consumed
  6. temperatureThe reaction mixture was cooled back to 0° C
  7. filtrationThe resulting slurry was filtered
  8. customto collect the N-oxide as the meta-chlorobenzoic acid salt
  9. washThe solid was washed with additional EtOAc
  10. customdried under vacuum

Sources & evidence

ORD record
ord-6011dc26a0914afe87d1305875dbafe5
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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