Water → 4-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridine

HRID 79550Notes

Reaction equation

HRID 79550 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]=[C:4]2[N:14](S(C3C=CC=CC=3)(=O)=O)[CH:15]=[CH:16][C:3]=12.C1COCC1.O.[Li+].[OH-]>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]=[C:4]2[NH:14][CH:15]=[CH:16][C:3]=12

Participants

6

Reactant 4

HCID 962Water2×HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68762479HCID 68762479, compound

Product 1

HCID 687625794-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridineYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

4-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.70 g, 4.61 mmol) was placed in 1:1 THF:water (30 mL). 3M LiOH (aq., 15.4 mL, 46.1 mmol) was then added, and the reaction was heated to 65° C. for 18 hours. The reaction was cooled to room temperature, diluted with DCM (50 mL) and poured into water. The organic fraction was dried, filtered, and concentrated to give the crude product 4-chloro-5-phenyl-1H-pyrrolo[2,3-b]pyridine (1.01 g, 95.8% yield), which was used without further purification.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe organic fraction was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-566720c2359d445b9ea60335782a9a2a
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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