Hydrochloric Acid → 8-Bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one

HRID 857336Notes

Reaction equation

HRID 857336 reaction equation
[Br:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14](=[O:15])[CH:13](C(OC)=O)[CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([F:11])[CH:10]=1.Cl.O>CCO>[Br:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14](=[O:15])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([F:11])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58760711Methyl 8-bromo-6-fluoro-1-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate

Product 1

HCID 218674218-Bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-oneYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the ketoester of Step 5 (4 g) in EtOH (150 mL) r.t. was added 40 mL of concentrated HCl. The reaction mixture was stirred at reflux for 1 hour and water was added. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were concentrated The residue was swished in EtOAc/Hexanes to provide 2.9 g of the title compound as a pale yellow solid.

Workup

  1. temperatureat reflux for 1 hour
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. concentrationthe combined organic layers were concentrated The residue

Sources & evidence

ORD record
ord-3f97eba8f7f144abb88a9df47f0f5270
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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