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

HRID 1024193Notes

Reaction equation

HRID 1024193 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[N:16]=[CH:15][C:14]([C:17](Cl)=[O:18])=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Cl:10][C:11]1[N:16]=[CH:15][C:14]([C:17]([C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)=[O:18])=[CH:13][CH:12]=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-9bbb5b618d714c1b848278fa6657df6a
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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