Nitrogen → 4-Isoquinolinecarbonitrile

HRID 1470479ノート

反応式

HRID 1470479 の反応式
Br[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N#N.[CH3:14][N:15](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[C-]#N.[Zn+2]>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]([C:14]#[N:15])=[CH:2][N:3]=1

参加物

6

反応物 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 6409693-Bromoisoquinoline

生成物 1

HCID 964504-Isoquinolinecarbonitrile収率 27.4%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
120 °C

実験手順

To a stirred solution of 3-bromoisoquinoline (Intermediate-12) (9.2 g, 44.2 mmol) in DMF (15 mL) were added, Pd(PPh3)4 (10.2 g, 8.84 mmol) and Zn(CN)2 (10.34 g, 88.44 mmol, 2.0 eq) and the solution was degassed with N2 for 20 min. It was then heated to 120° C. overnight. After the completion (TLC), reaction mixture was cooled to RT, filtered and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (10% EtOAc:Hexanes) to afford the desired compound (3.4 g, 27.4%) as pale yellow solid.

後処理

  1. customAfter the completion (TLC), reaction mixture
  2. temperaturewas cooled to RT
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product obtained
  6. customwas purified by flash column chromatography (10% EtOAc:Hexanes)

出典と根拠

ORDレコード
ord-bcda7d7fa6fa4218b3098cdbb0913636
出典データセット
uspto-grants-2015_04
特許番号
US09006442B2

反応ノート

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