N-bromobutanimide → 3-Bromo-8-chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine

HRID 449036Notes

Reaction equation

HRID 449036 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:8]=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:31])C(=O)C1>CN(C=O)C>[Br:31][C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]2=[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[N:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866360348-Chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine

Product 1

HCID 866360333-Bromo-8-chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine (2.10 g, 6.5 mmol) in DMF (12 mL) at 0° C. was added NBS (1.40 g, 7.84 mmol) and stirred for 2 h. DMF was removed under pressure and added water (75 mL). Solid formed was extracted with EtOAc (3×50 mL), washed with water (40 mL) and dried (Na2SO4). Evaporation of solvent gave crude material, which was purified by column chromatography on silica gel using CH2Cl2/MeOH (98:2). Yield: 2.05 g (77%); 1H NMR (CDCl3, 300 MHz) δ 7.11-7.21 (m, 5H), 7.28-7.32 (m, 3H), 7.61-7.64 (m, 2H), 7.70 (d, J=2.4 Hz, 1H).

Workup

  1. customDMF was removed under pressure
  2. additionadded water (75 mL)
  3. customSolid formed
  4. extractionwas extracted with EtOAc (3×50 mL)
  5. washwashed with water (40 mL)
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of solvent
  8. customgave crude material, which
  9. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3e0d4a4dee4c4cbfa8780af51deba103
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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