Ethanol → 5-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-pyrrolo[1,2-a]indol-9-ylamine

HRID 1925574Notes

Reaction equation

HRID 1925574 reaction equation
[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH:3][C:2]=1[C:10]1[C:18]2[N:17]3[CH:19]=[CH:20][CH:21]=[C:16]3[C:15](=[N:22]O)[C:14]=2[CH:13]=[CH:12][CH:11]=1.C(O)C.O>C(O)(=O)C.[Zn]>[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH:3][C:2]=1[C:10]1[C:18]2[N:17]3[CH:19]=[CH:20][CH:21]=[C:16]3[CH:15]([NH2:22])[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 866560785-(3H-imidazo[4,5-c]pyridin-2-yl)pyrrolo[1,2-a]indol-9-one oxime

Product 1

HCID 670728065-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-pyrrolo[1,2-a]indol-9-ylamineYield 26.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

In a 100 ml round-bottomed flask, a mixture of 200 mg of 5-(3H-imidazo[4,5-c]pyridin-2-yl)pyrrolo[1,2-a]indol-9-one oxime obtained according to the preceding stage, in 5 ml of glacial acetic acid, 5 ml of ethanol and 5 ml of water, is stirred at ambient temperature. 43 mg of powdered zinc are added and the stirring is maintained at ambient temperature for 2 hours. The reaction medium is filtered through clarcel, washing being carried out with methanol. The filtrate is evaporated to dryness under vacuum and the residue is chromatographed on silica gel (15-40 μm), elution being carried out with a mixture of dichloromethane and 5N ammoniacal methanol (95/5 v/v). 51 mg of 5-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-pyrrolo[1,2-a]indol-9-ylamine are obtained in the form of a solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. filtrationThe reaction medium is filtered through clarcel
  3. washwashing
  4. customThe filtrate is evaporated to dryness under vacuum
  5. customthe residue is chromatographed on silica gel (15-40 μm), elution
  6. additionbeing carried out with a mixture of dichloromethane and 5N ammoniacal methanol (95/5 v/v)

Sources & evidence

ORD record
ord-7195230bd3b7442ba673aff87538457b
Source dataset
uspto-grants-2012_05
Patent number
US08178687B2

Reaction notes

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