1H-Pyrrolo(2,3-b)pyridine → 7-aza-1H-indole N-oxide

HRID 2182245Notes

Reaction equation

HRID 2182245 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1>ClCCl>[NH+:12]1([O-:9])[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1

Participants

4

Reactant 2

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

Product 1

HCID 219590977-aza-1H-indole N-oxideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroperbenzoic acid (224.3 g) in dichloromethane (1500 mL) was cooled to 0° C. To this a solution of 1H-pyrrolo[2,3-b]pyridine (59.1 g) in dichloromethane (500 mL) was added dropwise over 30 minutes. The reaction mixture was stirred at room temperature for 1 hour. The solution was concentrated, diluted with methanol (1500 mL) and treated with 10% potassium carbonate in water (300 mL). The slurry was filtered and the filtrate was evaporated to dryness. The residue was chromatographed on neutral alumina with 20% methanol in dichloromethane to give the title compound as a tan solid (47.0 g). MS: 135(MH+). 1HNMR (CDCl3): δ 13.1 (s, 1H), 8.2 (d, 1H), 7.65 (d, 1H), 7.4 (d, 1H), 7.0 (m, 1H), 6.55 (d, 1H).

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with methanol (1500 mL)
  3. additiontreated with 10% potassium carbonate in water (300 mL)
  4. filtrationThe slurry was filtered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was chromatographed on neutral alumina with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-ae6b2ac03b484bd9a871b79ce5117d2e
Source dataset
uspto-grants-2005_05
Patent number
US06897207B2

Reaction notes

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