9-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid (2-amino-4-fluorophenyl)amide → 5-(6-fluoro-1H-benzimidazol-2-yl)pyrrolo[1,2-a]indol-9-one

HRID 1925564Notes

Reaction equation

HRID 1925564 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[N:19]1[CH:21]=[CH:22][CH:23]=[C:18]1[C:17]2=[O:24])=O>C(O)(=O)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]=[C:10]([C:12]3[C:20]4[N:19]5[CH:21]=[CH:22][CH:23]=[C:18]5[C:17](=[O:24])[C:16]=4[CH:15]=[CH:14][CH:13]=3)[NH:1][C:2]=2[CH:7]=1

Participants

3

Reactant 1

HCID 672992369-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid (2-amino-4-fluorophenyl)amide

Product 1

HCID 670729195-(6-fluoro-1H-benzimidazol-2-yl)pyrrolo[1,2-a]indol-9-oneYield 33.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 250 ml round-bottomed flask, a mixture of 375 mg of 9-oxo-9H-pyrrolo[1,2-a]indole-5-carboxylic acid (2-amino-4-fluorophenyl)amide obtained according to the preceding stage, in 40 ml of glacial acetic acid, is refluxed for 3 hours. The reaction medium is evaporated to dryness under vacuum and the residue is chromatographed on silica gel (15-40 μm), elution being carried out with a gradient of methanol (0 to 30% by volume) in dichloromethane. 119 mg of 5-(6-fluoro-1H-benzimidazol-2-yl)pyrrolo[1,2-a]indol-9-one are obtained in the form of a yellowish solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. temperatureis refluxed for 3 hours
  3. customThe reaction medium is evaporated to dryness under vacuum
  4. customthe residue is chromatographed on silica gel (15-40 μm), elution

Sources & evidence

ORD record
ord-af3cefa7e7c94aa4950126286c25f4e2
Source dataset
uspto-grants-2012_05
Patent number
US08178687B2

Reaction notes

Loading…