1H-Pyrrolo(2,3-b)pyridine → HCID 178526243, compound

HRID 1396361Notes

Reaction equation

HRID 1396361 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.ClC1C=CC=C(C(OO)=[O:18])C=1>C(OCC)(=O)C>[NH:1]1[C:5]2=[N+:6]([O-:18])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

4

Reactant 2

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

Product 1

HCID 178526243HCID 178526243, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

1H-pyrrolo[2,3-b]pyridine (2.8 g, 24 mmol) was dissolved in ethyl acetate (24 mL) and cooled to 0° C. A solution of 3-chloroperbenzoic acid (77%, 6.7 g, 30.1 mmol) in ethyl acetate (24 mL) was added drop-wise then the reaction mixture warmed to 25° C. over 16 h. The reaction mixture was cooled to 0° C., filtered, and the solids dried to give crude 1H-pyrrolo[2,3-b]pyridine 7-oxide, 3-chlorobenzoic acid complex (4.1 g, 58%) as an off-white solid. This was used directly in the next step without purification. LCMS (EI/CI) m/z: 135 [M+H].

Workup

  1. temperaturethe reaction mixture warmed to 25° C. over 16 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationfiltered
  4. customthe solids dried

Sources & evidence

ORD record
ord-f24c7f49a97247b1af511e3a94b25ea8
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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