Sodium Carbonate → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 491649Notes

Reaction equation

HRID 491649 reaction equation
O=P(Cl)(Cl)[Cl:3].[NH:6]1[C:10]2=[N+:11]([O-])[CH:12]=[CH:13][CH:14]=[C:9]2[CH:8]=[CH:7]1.C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:3][C:14]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:6][CH:7]=[CH:8][C:9]=12

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178526243HCID 178526243, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To cooled POCl3 (50 mL) in a dried round bottom flask, 1H-pyrrolo[2,3-b]pyridine 7-oxide (6.6 g, step A) was added in portions. The mixture was heated to reflux for 5 h. After cooling to RT, POCl3 was evaporated under high vacuum with gentle heating (40-50° C.) to obtain a black residue. Water (50 mL) was added slowly and the pH was adjusted to 8-9 with Na2CO3 (first with solid, then saturated aqueous solution). The resulting precipitate was collected by filtration, washed with cold H2O and dried in a vacuum oven (50° C.) to give 4-chloro-1H-pyrrolo[2,3-b]pyridine as a tan powder. This was a mixture of desired product and a regioisomer, which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 h
  3. customPOCl3 was evaporated under high vacuum
  4. temperaturewith gentle heating (40-50° C.)
  5. customto obtain a black residue
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with cold H2O
  8. customdried in a vacuum oven (50° C.)

Sources & evidence

ORD record
ord-ee9018ed420d4372999b8b7ea1440389
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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