Water → 2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 1929995Notes

Reaction equation

HRID 1929995 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=O.Cl.[NH:14]=[C:15]1[CH2:19][CH2:18][CH2:17][NH:16]1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:14]=[C:15]2[CH2:19][CH2:18][CH2:17][N:16]2[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27741852-Bromo-2',4'-difluoroacetophenoneHCID 178479085HCID 178479085, compound

Product 1

HCID 579298552-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazoleYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-1-(2,4-difluorophenyl)ethanone (7.05 g, 30.0 mmol, prepared using General Procedure A.1 from 1-(2,4-difluorophenyl)ethanone), 2-iminopyrrolidine hydrochloride (10.9 g, 90 mmol, prepared following the procedure in J. Med. Chem., 2002, 45, 999-1001) and Na2CO3 (21.1 g, 199 mmol) in DMF (30 mL) was stirred overnight at about 80° C. The reaction mixture was cooled to ambient temperature, poured into water, and extracted with EtOAc. The organics were dried over MgSO4, filtered and concentrated under reduced pressure to give the crude title compound (6.61 g, 100%): LC/MS (Table 1, Method a) Rt=2.72 min; MS m/z: 221.0 (M+H)+.

Workup

  1. customprepared
  2. extractionextracted with EtOAc
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-caf4c93ec4ed4b12ae69a951dcf4ab1d
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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