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

HRID 1634898노트

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HRID 1634898 반응식
[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]

참가 물질

8

반응물 2

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

생성물 1

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

시약·촉매·용매 5

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

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온도
45 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3d540c9f63c94badba83729f06af6a5a
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509329B1

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