Water → HCID 89826376, compound

HRID 2272974Notes

Reaction equation

HRID 2272974 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)=[O:15])[CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 74544-Bromophenacyl bromideHCID 10796Cesium carbonateHCID 72212396HCID 72212396, compound

Product 1

HCID 89826376HCID 89826376, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 15.7 g (100 mmol) 4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester and 27.8 g (100 mmol) 2,4′-dibromoacetophenone in 150 ml acetone is added 16.6 g (120 mmol) cesium carbonate. The resulting suspension is stirred at 35° C. for 3 days. The reaction mixture is added to 600 ml water under stirring. The resulting precipitate is filtered off, washed with water and dried under vacuum to afford 1-[2-(4-bromo-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester as light yellow solid; HPLC/MS 3.14 (B), [M+H] 354/356;

Workup

  1. stirringunder stirring
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-202bf1b40f6e4111b8c058b39896c620
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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