Phosphorus oxychloride → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 2211955Notes

Reaction equation

HRID 2211955 reaction equation
[NH:1]1[C:5]2=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526243HCID 178526243, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineYield 76%

Conditions

Temperature
80 °C

Procedure

1H-Pyrrolo[2,3-b]pyridine 7-oxide was added slowly to 200 mL POCl3 and the resulting mixture stirred at 80° C. overnight. The excess POCl3 was then removed in vacuo and the residue treated with 500 mL H2O and basified with saturated K2CO3 (aq), prior to extraction with EtOAc (2×300 mL). The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 4-Chloro-1H-pyrrolo[2,3-b]pyridine (12.9 g, 76%). MS (ES+): 153 [MH+].

Workup

  1. customThe excess POCl3 was then removed in vacuo
  2. additionthe residue treated with 500 mL H2O and basified with saturated K2CO3 (aq)
  3. extractionto extraction with EtOAc (2×300 mL)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c75139fc7943408c873ab856a54af51b
Source dataset
uspto-grants-2006_09
Patent number
US07101893B2

Reaction notes

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