Dimethylacetamide → 5-Amino-6-methylpicolinonitrile

HRID 2377580ノート

反応式

HRID 2377580 の反応式
Br[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.[CH3:10][N:11](C)C(=O)C>C(OCC)(=O)C.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].[Zn].[C-]#N.[Zn+2].[C-]#N>[C:10]([C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][CH:3]=1)#[N:11]

参加物

7

反応物 2

HCID 31374DimethylacetamideHCID 144180456-Bromo-2-methylpyridin-3-amine

生成物 1

HCID 552529845-Amino-6-methylpicolinonitrile

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

A mixture of 3.5 g (18.6 mmol) of 6-bromo-2-methyl-3-aminopyridine, 352 mg (0.37 mmol) of tris(benzylideneacetone)dipalladium(0), 532 mg (0.92 mmol) of 1,1′-bis(diphenylphosphino)ferrocene, 146 mg (2.2 mmol) of zinc powder and 1.4 g (12 mmol) of zinc cyanide in 70 ml of N,N-dimethylacetamide is prepared and the reaction mixture is then stirred at 20° C. for 22 hours. It is diluted with 200 ml of ethyl acetate and washed with 2 N ammonium chloride solution. (Decantation is obtained only after filtration of the mixture on a filter aid of the Celite type.) The organic phase obtained is washed with sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (9/1; v/v) as the eluent to give 1.6 g of the expected compound in the form of a yellow powder (yield=65%).

後処理

  1. customis prepared
  2. washwashed with 2 N ammonium chloride solution
  3. custom(Decantation is obtained only
  4. filtrationafter filtration of the mixture on a filter aid of the Celite type
  5. custom) The organic phase obtained
  6. washis washed with sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (9/1; v/v) as the eluent

出典と根拠

ORDレコード
ord-6bcb82fab73a44e7924690ebf7c8852c
出典データセット
uspto-grants-2008_12
特許番号
US07470671B2

反応ノート

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