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

HRID 1441818ノート

反応式

HRID 1441818 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 218749014-Bromoisoquinoline-1-carbonitrile収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7bcec234d2694ff188847778d5eabdfe
出典データセット
uspto-grants-2010_02
特許番号
US07655689B2

反応ノート

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