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

HRID 723681ノート

反応式

HRID 723681 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-d76da83532134080a39468ad859c2c55
出典データセット
uspto-grants-2006_11
特許番号
US07141578B2

反応ノート

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