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

HRID 422287Notes

Reaction equation

HRID 422287 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent2×

Procedure

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 string 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 20 h 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.

Workup

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

Sources & evidence

ORD record
ord-31d519ad7854456cab3226bc9c68560f
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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