1H-Pyrrolo(2,3-b)pyridine → (6-Chloro-pyridin-3-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 1367306Notes

Reaction equation

HRID 1367306 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][N:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Cl:10][C:11]1[N:12]=[CH:13][C:14]([C:15]([C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)=[O:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 27821656-Chloronicotinoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 57588066(6-Chloro-pyridin-3-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 7-azaindole 1 in dichloromethane was added 6-chloronicotinoyl chloride 8, followed by aluminum chloride, under an atmosphere of nitrogen at −10° C. The reaction was stirred and allowed to warm to room temperature overnight. The reaction was quenched with 3 N hydrochloric acid and concentrated hydrochloric acid was added until all solids dissolved. The mixture was extracted with dichloromethane and the combined organic portions were dried with magnesium sulfate, filtered, and the filtrate was concentrated. The resulting solid material was recrystallized from chloroform/hexane to provide (6-Chloro-pyridin-3-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone 7 and used in the next step without further purification.

Workup

  1. customThe reaction was quenched with 3 N hydrochloric acid and concentrated hydrochloric acid
  2. additionwas added until all solids
  3. dissolutiondissolved
  4. extractionThe mixture was extracted with dichloromethane
  5. dry with materialthe combined organic portions were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe resulting solid material was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-02de8855da184a3e9708d8f3cf6a45ab
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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