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

HRID 1441818노트

반응식

HRID 1441818 반응식
[N:1]12CCCN=C1CCCC[CH2:2]2.[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:2]#[N:1])=[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

1,8-Diazabicyclo[5.4.0]undec-7-ene (1.67 mL, 11.2 mmol) was added to a mixture of compound 470A (1.12 g, 5.00 mmol) and cyanotrimethylsilane (0.75 mL, 5.5 mmol) in 35 mL of THF. The resulting homogeneous mixture was refluxed for 20 min. After concentrating in vacuo, the residue was purified by flash chromatography on a 5×15 cm silica gel column, eluting with 3:1 hexane:ethyl acetate to give 0.95 g (82%) of compound 470B as a white powder. 1H NMR (400 MHz, CDCl3): δ 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 in vacuo
  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-7bcec234d2694ff188847778d5eabdfe
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655689B2

반응 노트

불러오는 중…