Nitrogen → 4-Isoquinolinecarbonitrile

HRID 1470479노트

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HRID 1470479 반응식
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

참가 물질

6

반응물 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 6409693-Bromoisoquinoline

생성물 1

HCID 964504-Isoquinolinecarbonitrile수율 27.4%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bcda7d7fa6fa4218b3098cdbb0913636
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006442B2

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