Dimethylformamide → 3-Amino-5-(trifluoromethyl)pyridine-2-carbonitrile

HRID 1775270ノート

反応式

HRID 1775270 の反応式
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:13][N:14](C=O)C.C(OCC)(=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[NH2:1][C:2]1[C:3]([C:13]#[N:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

参加物

8

反応物 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 129197572-Chloro-5-(trifluoromethyl)pyridin-3-amine

生成物 1

HCID 135322513-Amino-5-(trifluoromethyl)pyridine-2-carbonitrile

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

A mixture of 5.14 g of 3-amino-2-chloro-5-trifluoromethylpyridine, 3.92 g of zinc cyanide, 1.19 g of tris(dibenzylideneacetone)dipalladium(0), 1.45 g of 1,1′-bis(diphenylphosphino)ferrocene and 20 ml of DMF was stirred at 150° C. for 40 minutes. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate, then combined with the organic layer of the filtrate and washed with water, and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, and then the resulting residue was applied to a silica gel column chromatography to obtain 2.23 g of 3-amino-2-cyano-5-trifluoromethylpyridine.

後処理

  1. filtrationthe mixture was filtered
  2. extractionThe aqueous layer of the filtrate was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe mixture was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-d4aa2b84fb7b4aea933d1f76df081531
出典データセット
uspto-grants-2016_02
特許番号
US09260436B2

反応ノート

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