N-bromobutanimide → 3-Bromo-2-(4-fluorophenyl)imidazo[1,2-a]pyrazine

HRID 2233077Notes

Reaction equation

HRID 2233077 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[N:14][CH:13]=[CH:12][N:11]3[CH:16]=2)=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)Cl>[Br:17][C:16]1[N:11]2[CH:12]=[CH:13][N:14]=[CH:15][C:10]2=[N:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 32311372-(4-Fluorophenyl)imidazo[1,2-a]pyrazine

Product 1

HCID 498448783-Bromo-2-(4-fluorophenyl)imidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-fluorophenyl)imidazo[1,2-a]pyrazine (Preparation #2, 0.176 g, 0.783 mmol) in DCM (3 mL) was added N-bromosuccinimide (0.153 g, 0.862 mmol) dropwise. After about 20 minutes, the mixture was concentrated under reduced pressure and purified by flash silica gel chromatography using EtOAc as the eluent to yield the title compound (0.130 g, 54%>: LC/MS (Table 1, Method a) Rt=2.0 min; MS m/z: 294.2 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. custompurified by flash silica gel chromatography

Sources & evidence

ORD record
ord-53fd89d613044b3ea6bca610ac9040f4
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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