5-Azaindole → HCID 90094001, compound

HRID 1753058Notes

Reaction equation

HRID 1753058 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][N:23]=1)[C:18](Cl)=[O:19].[OH-].[Na+]>ClCCCl.CO>[Cl:14][C:15]1[CH:16]=[C:17]([C:18]([C:3]2[C:4]3[CH:5]=[N:6][CH:7]=[CH:8][C:9]=3[NH:1][CH:2]=2)=[O:19])[CH:21]=[CH:22][N:23]=1

Participants

7

Reactant 4

HCID 92205-AzaindoleHCID 14798Sodium HydroxideHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 90094001HCID 90094001, compoundYield 122%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 887MethanolSolvent

Procedure

To a solution of 1H-pyrrolo[3,2-c]pyridine (17.0 g, 0.14 mol) in 1, 2-dichloroethane (500 mL) was added AlCl3 (38.3 g, 0.29 mol) at room temperature. The mixture was stirred at room temperature for 10 minutes. A solution of 2-chloroisonicotinoyl chloride (30.0 g, 0.17 mol) in 1, 2-dichloroethane (100 mL) was added and the reaction heated to 70° C. Further AlCl3 (38.3 g, 0.29 mol) was added and the reaction was stirred at this temperature for 18 hours. The mixture was cooled to room temperature, and then to the mixture was added MeOH (150 mL) dropwise. 1M aqueous NaOH solution was added until pH=8. The mixture was filtered, the filter cake was washed with a mixture of 1/3 isopropanol/chloroform and the filtrate was extracted with a mixture of 1/3 isopropanol/chloroform (300 mL×6). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give the title compound (44 g) as a black solid, which was used in next step directly.

Workup

  1. temperaturethe reaction heated to 70° C
  2. stirringthe reaction was stirred at this temperature for 18 hours
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with a mixture of 1/3 isopropanol/chloroform
  6. extractionthe filtrate was extracted with a mixture of 1/3 isopropanol/chloroform (300 mL×6)
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e520bf8d99204a59b262dd75b280ee42
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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