N-bromobutanimide → 3-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

HRID 1046993ノート

反応式

HRID 1046993 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.[Br:19]N1C(=O)CCC1=O>C1COCC1>[Br:19][C:3]1[N:4]2[C:5]3[CH:18]=[CH:17][CH:16]=[N:15][C:6]=3[NH:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[C:10]2=[N:1][CH:2]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 675031859H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

生成物 1

HCID 675039063-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine (1.19 g, 5.1 mmol) in THF (60 mL) was slowly added N-bromosuccinimide (0.90 g, 4.3 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hours, quenched with sat.NaHCO3, extracted with ethyl acetate. The organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography (hexane/ethyl acetate) to give a pale yellow solid (96%). 1H NMR (DMSO-d6) 400 MHz δ: 8.58 (s, 1H), 8.26 (dd, J=4.9, 1.4 Hz, 1H), 7.94 (dd, J=8.0, 1.7 Hz, 1H), 7.74 (dd, J=7.7, 1.4 Hz, 1H), 7.43 (s, 1H), 7.34 (td, J=7.7, 1.9 Hz, 1H), 7.25-7.21 (m, 2H), 7.08 (td, J=7.5, 1.2 Hz, 1H); LC/MS [M+H]: 314.

後処理

  1. customat 0° C
  2. customquenched
  3. extractionNaHCO3, extracted with ethyl acetate
  4. washThe organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed under reduced pressure
  8. customThe crude product was purified by silica gel chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-77066993abcb4f3eab07d9a9719da7fc
出典データセット
uspto-grants-2013_10
特許番号
US08569331B2

反応ノート

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