Sodium Cyanide → Indole-5-carbonitrile

HRID 710293

반응식

HRID 710293 반응식
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C-:11]#[N:12].[Na+]>CC#N.CCOC(C)=O.[Cu]I>[C:11]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)#[N:12]

참가 물질

6

반응물 2

HCID 8929Sodium CyanideHCID 27823135-Iodo-1H-indole

생성물 1

HCID 27513Indole-5-carbonitrile수율 95.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 5-iodoindole (0.36 g; 1.48 mmol), NaCN (0.15 g; 3 mmol), Pd(Ph3)4 (0.23 g; 0.22 mmol) and CuI (0.06 g; 0.3 mmol) in anhydrous CH3CN (3 ml) was refluxed for 2.5 h under N2. After cooling to room temperature, the mixture was diluted to 20 ml with EtOAc and filtered through a pad of Celite. The filtrate was washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure, dissolved in a small volume of CH2Cl2 and filtered through a small pad of SiO2, which was washed with fresh CH2Cl2. The combined filtrates were evaporated to dryness under reduced pressure to give the title compound (0.2 g; 95%) as colourless solid. 1H-NMR (CDCl3) 6.62 (tr, 1H, J=2.5 Hz); 7.33 (tr, 1H, J=2.5 Hz); 7.39-7.47 (m, 2H); 7.98 (s, 1H); 8.51 (broad s, 1H).

후처리

  1. temperaturewas refluxed for 2.5 h under N2
  2. filtrationfiltered through a pad of Celite
  3. washThe filtrate was washed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. dissolutiondissolved in a small volume of CH2Cl2
  8. filtrationfiltered through a small pad of SiO2, which
  9. washwas washed with fresh CH2Cl2
  10. customThe combined filtrates were evaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-06aff8e3d2e940f5acd987d69ad40d19
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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