Ethyl 2-chloroisonicotinate → Ethyl 2-(3,4,5-trimethoxyphenylethynyl)pyridine-4-carboxylate

HRID 1634898ノート

反応式

HRID 1634898 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[CH:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl[C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][N:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.C(N(CC)CC)C.C(OCC)(=O)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]#[C:14][C:16]2[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:24]=[CH:25][N:26]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

参加物

8

反応物 2

HCID 2762942Ethyl 2-chloroisonicotinateHCID 118302605-Ethynyl-1,2,3-trimethoxybenzene

生成物 1

HCID 18674974Ethyl 2-(3,4,5-trimethoxyphenylethynyl)pyridine-4-carboxylate

試薬・触媒・溶媒 5

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

3,4,5-Trimethoxyphenylacetylene (1.80 g), ethyl 2-chloroisonicotinate (2.08 g) and copper iodide (71 mg) were dissolved in a mixed solvent of DMF (4 mL) and triethylamine (8 mL), and to the solution bis-(triphenylphosphine)palladium dichloride (0) (131 mg) was added, and the mixture was stirred at 45° C. for 4 hours under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate. After concentrating the reaction mixture under reduced pressure, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 to 3:1) to obtain the title compound.

後処理

  1. washwashed with 2 M hydrochloric acid, water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationAfter concentrating the reaction mixture under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 to 3:1)

出典と根拠

ORDレコード
ord-3d540c9f63c94badba83729f06af6a5a
出典データセット
uspto-grants-2003_01
特許番号
US06509329B1

反応ノート

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