9-Oxofluorene-4-carboxylic acid → HCID 67360748, compound

HRID 2243336Notes

Reaction equation

HRID 2243336 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH-:9].[O:10]=[C:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([C:24](O)=O)[C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2>C(O)(=O)C>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]=[C:24]([C:19]3[C:18]4[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[C:11](=[O:10])[C:23]=4[CH:22]=[CH:21][CH:20]=3)[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 803619-Oxofluorene-4-carboxylic acidHCID 86621035HCID 86621035, compound

Product 1

HCID 67360748HCID 67360748, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.61 g of (2-amino-4-bromophenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid in 80 ml of glacial acetic acid is refluxed for 2.5 hours. Allow to return to ambient temperature and evaporate the reaction medium to dryness under vacuum. The residue is taken up with 50 ml of dichloromethane, and the organic phase is washed with twice 50 ml of a saturated solution of sodium bicarbonate and 50 ml of a saturated solution of sodium chloride. After drying over magnesium sulphate, the organic phase is evaporated to dryness under vacuum. The residue is chromatographed on silica gel, eluting with a mixture of methanol and dichloromethane (5/95 by volume). In this way, we obtain 1.5 g of 4-(6-bromo-1H-benzimidazol-2-yl)-9H-fluoren-9-one, with the following characteristics:

Workup

  1. temperatureis refluxed for 2.5 hours
  2. customto return to ambient temperature
  3. customevaporate the reaction medium to dryness under vacuum
  4. washthe organic phase is washed with twice 50 ml of a saturated solution of sodium bicarbonate and 50 ml of a saturated solution of sodium chloride
  5. dry with materialAfter drying over magnesium sulphate
  6. customthe organic phase is evaporated to dryness under vacuum
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a mixture of methanol and dichloromethane (5/95 by volume)

Sources & evidence

ORD record
ord-c5ee04c37a284078aba04a50052ac798
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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