1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Bromoisoquinoline-1-carbonitrile

HRID 501544노트

반응식

HRID 501544 반응식
C1CCN2[C:4](=[N:5]CCC2)CC1.[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[N+:15]([O-])[CH:14]=1.C([Si](C)(C)C)#N>C1COCC1>[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:4]#[N:5])=[N:15][CH:14]=1

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82115Trimethylsilyl cyanideHCID 8173234-Bromoisoquinoline N-oxide

생성물 1

HCID 218749014-Bromoisoquinoline-1-carbonitrile수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

DBU (1.67 mL, 11.2 mmol) was added to a mixture of compound 13A (1.12 g, 5.00 mmol) and cyanotrimethylsilane (0.75 mL, 5.5 mmol) in THF (35 mL). The resulting homogeneous mixture was refluxed for 20 min. After concentrating under reduced pressure, the residue was purified by flash chromatography on a 5×15 cm silica gel column, eluting with 3:1 hexane:EtOAc to give compound 13B (0.95 g, 82%) as a white powder. 1H NMR (400 MHz, CDCl3) □8.85 (s, 1H), 8.36 (d, 1H, J=8.5 Hz), 8.28 (d, 1H, J=8.5 Hz), 7.96 (t, 1H, J=8.5 Hz), 7.89 (t, 1H, J=8.5 Hz).

후처리

  1. temperatureThe resulting homogeneous mixture was refluxed for 20 min
  2. concentrationAfter concentrating under reduced pressure
  3. customthe residue was purified by flash chromatography on a 5×15 cm silica gel column
  4. washeluting with 3:1 hexane

출처 및 근거

ORD 기록
ord-1c7c03fc252c4dad87e067f54138d560
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772267B2

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