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

HRID 449036ノート

反応式

HRID 449036 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3e0d4a4dee4c4cbfa8780af51deba103
出典データセット
uspto-grants-2013_07
特許番号
US08481733B2

反応ノート

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