Dimethylacetamide → 1H-Pyrrolo[2,3-B]pyridine-4-carbonitrile, 1-[(4-methylphenyl)sulfonyl]-

HRID 506797ノート

反応式

HRID 506797 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12.[CH3:21][N:22](C)C(=O)C>[C-]#N.[Zn+2].[C-]#N.[Zn].Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:21]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12)#[N:22]

参加物

7

反応物 2

HCID 31374DimethylacetamideHCID 81672684-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 224772881H-Pyrrolo[2,3-B]pyridine-4-carbonitrile, 1-[(4-methylphenyl)sulfonyl]-

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒HCID 24290Palladium Chloride触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒

反応条件

温度
140 °C

実験手順

To a solution of 10 g of 4-chloro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in 200 cm3 of N,N-dimethylacetamide, under an inert atmosphere of argon, are added 6.9 g of zinc cyanide and 1.07 g of zinc powder. After stirring for 45 minutes at a temperature in the region of 20° C., 2.4 g of PdCl2, dppf are added. The reaction medium is heated at a temperature in the region of 140° C. for 1 hour 30 minutes. After cooling, the reaction medium is filtered through Celite and then rinsed with dichloromethane. 150 cm3 of water are added to the filtrate. After separation of the phases by settling, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. After purification by flash chromatography on a column (SiO2, cyclohexane/ethyl acetate, 75/25 by volume as eluent, Ar), 8.57 g of 4-cyano-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine are obtained with the following characteristics:

後処理

  1. additionare added
  2. temperatureAfter cooling
  3. filtrationthe reaction medium is filtered through Celite
  4. washrinsed with dichloromethane
  5. addition150 cm3 of water are added to the filtrate
  6. customAfter separation of the phases
  7. dry with materialthe organic phase is dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customAfter purification by flash chromatography on a column (SiO2, cyclohexane/ethyl acetate, 75/25 by volume as eluent, Ar), 8.57 g of 4-cyano-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine
  11. customare obtained with the following characteristics

出典と根拠

ORDレコード
ord-0d3fda9691084f2aba40fab49931e730
出典データセット
uspto-grants-2010_08
特許番号
US07786114B2

反応ノート

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