Water → HCID 71765086, compound

HRID 2272975Notes

Reaction equation

HRID 2272975 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)=O)[CH:8]=[C:9]([F:11])[CH:10]=1)=O)C.C([O-])(=O)C.[NH4+:26].O>C(O)(=O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[NH:26][C:4](=[O:3])[C:6]3[N:7]([CH:8]=[C:9]([F:11])[CH:10]=3)[CH:12]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 89826376HCID 89826376, compound

Product 1

HCID 71765086HCID 71765086, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 27.4 g (77.3 mmol) 1-[2-(4-bromo-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester and 140 g (1.82 mol) ammonium acetate in 150 ml acetic acid is heated to 110° C. and the resulting solution is stirred for 18 hours at 110° C. The reaction mixture is allowed to cool to room temperature and added to 1.5 I water under stirring. The resulting precipitate is filtered off, washed with water and dried under vacuum. It is taken up in isopropyl acetate, heated to reflux and filtered while hot. The residue is washed with isopropyl acetate and dried under vacuum to afford 3-(4-bromo-phenyl)-7-fluoro-2H-pyrrolo[1,2-a]pyrazin-1-one as grey crystals; HPLC/MS 1.83 min (A), [M+H] 307/309;

Workup

  1. temperatureto cool to room temperature
  2. stirringunder stirring
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with water
  5. customdried under vacuum
  6. temperatureheated
  7. temperatureto reflux
  8. filtrationfiltered while hot
  9. washThe residue is washed with isopropyl acetate
  10. customdried under vacuum

Sources & evidence

ORD record
ord-cdcc79e7b917457e9903b86da34cb185
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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