2-Iodopyridine → 2-(4-(3-(2-Methoxyphenyl)-1,2,4-oxadiazol-5-yl)but-1-ynyl)pyridine

HRID 1189087노트

반응식

HRID 1189087 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[N:13]=1)[CH2:9][C:10]#[CH:11]>C(N(CC)CC)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>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[N:13]=[C:12]([CH2:8][CH2:9][C:10]#[C:11][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[O:16][N:15]=1

참가 물질

6

반응물 2

HCID 2211262-IodopyridineHCID 860867965-(But-3-ynyl)-3-(2-methoxyphenyl)-1,2,4-oxadiazole

생성물 1

HCID 115077712-(4-(3-(2-Methoxyphenyl)-1,2,4-oxadiazol-5-yl)but-1-ynyl)pyridine수율 13%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매2회

실험 절차

In a dry reaction tube containing in suspension copper iodide (12 mg, 0.07 mmol) and triethylamine (4.1 mL, 29 mmol), were added 2-iodopyridine (139 μL, 1.3 mmol) and Pd(PPh3)2Cl2 (46 mg, 0.07 mmol) under N2. A yellow suspension is obtained and after a few minutes of stiffing at room temperature, was added a solution 5-(but-3-ynyl)-3-(2-methoxyphenyl)-1,2,4-oxadiazole (299 mg, 1.3 mmol) in triethylamine (0.7 mL) under N2. Immediately the color of the reaction turns to black. The mixture was stirred at room temperature for 20h under N2. Triethylamine was removed under reduce pressure and the crude product was purified by flash chromatography (Prepacked column 10 g, cyclohexane/AcOEt: from 60/40 to 50/50 as eluent) to afford 50 mg of 2-(4-(3-(2-methoxyphenyl)-1,2,4-oxadiazol-5-yl)but-1-ynyl)pyridine (13%) as brown oil.

후처리

  1. customIn a dry reaction tube
  2. customA yellow suspension is obtained and after a few minutes
  3. customof stiffing at room temperature
  4. customTriethylamine was removed
  5. customthe crude product was purified by flash chromatography (Prepacked column 10 g, cyclohexane/AcOEt: from 60/40 to 50/50 as eluent)

출처 및 근거

ORD 기록
ord-d043ff7e57074aaaa13aec60c4ecf594
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674106B2

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