Sodium Cyanide → Indole-5-carbonitrile

HRID 710293

反応式

HRID 710293 の反応式
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]

参加物

6

反応物 2

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

生成物 1

HCID 27513Indole-5-carbonitrile収率 95.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-06aff8e3d2e940f5acd987d69ad40d19
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

関連ノート

読み込み中…