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

HRID 1046993노트

반응식

HRID 1046993 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-77066993abcb4f3eab07d9a9719da7fc
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569331B2

반응 노트

불러오는 중…