HCID 178418260、化合物 → HCID 178470417、化合物

HRID 33239

反応式

HRID 33239 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:10]=1I)=[O:5])[CH3:2].[Cu](C#N)[C:18]#[N:19]>[C-]#N.C([N+](CC)(CC)CC)C.CN(C=O)C.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]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:10]=1[C:18]#[N:19])=[O:5])[CH3:2]

参加物

7

反応物 2

HCID 178418260HCID 178418260、化合物HCID 178470418HCID 178470418、化合物

生成物 1

HCID 178470417HCID 178470417、化合物

試薬・触媒・溶媒 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 3014735Tetraethylammonium cyanide触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

1.57 g (4.5 mmol) of 4-Iodo-5-thiophen-2-yl-2H-pyrazole-3-carboxylic acid ethyl ester, 0.81 g (9.0 mmol) of copper cyanide and 352 mg (2.3 mmol) of tetraethylammonium cyanide were dissolved in 10 ml of DMF and 20 ml of tetrahydrofuran and the solution was degassed with argon. 223 mg (0.2 mmol) of Tris(dibenzylideneacetone)dipalladium (0) and 374 mg (0.7 mmol) of 1,1′-bis-(diphenylphosphino) ferrocene were added at RT. The reaction was stirred at 120° C. for 5 h. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and this solution was washed with saturated aqueous sodium bicarbonate. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography eluting with n-heptane:ethyl acetate/1:1.

後処理

  1. custom20 ml of tetrahydrofuran and the solution was degassed with argon
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthis solution was washed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by silica gel chromatography
  9. washeluting with n-heptane

出典と根拠

ORDレコード
ord-0f32fbdb35bc46b399bc692733142482
出典データセット
uspto-grants-2008_09
特許番号
US07429581B2

関連ノート

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