3-Fluoro-2-iodopyridine → 2-(4-(3-Fluoropyridin-2-yl)but-3-ynyl)benzo[d]oxazole

HRID 334792Notes

Reaction equation

HRID 334792 reaction equation
[F:1][C:2]1[C:3](I)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]([C:13]1[O:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)[CH2:10][C:11]#[CH:12]>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>[F:1][C:2]1[C:3]([C:12]#[C:11][CH2:10][CH2:9][C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 15194833-Fluoro-2-iodopyridineHCID 860869072-(But-3-ynyl)benzo[d]oxazole2×

Product 1

HCID 666755842-(4-(3-Fluoropyridin-2-yl)but-3-ynyl)benzo[d]oxazoleYield 15.2%

Reagents, catalysts & solvents 3

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

Procedure

In a dry reaction tube containing in suspension copper iodide (28 mg, 0.148 mol) and triethylamine (8.30 mL, 59.20 mmol), were added 3-fluoro-2-iodopyridine (660 mg, 2.96 mmol) and Pd(PPh3)2Cl2 (104 mg, 0.148 mmol) under N2. A yellow suspension was obtained. After a 5 minutes of stirring at room temperature, was added a solution 2-(But-3-ynyl)benzo[d]oxazole (compound 8(A), 510 mg, 3 mmol) in triethylamine (0.2 mL) under N2. Immediately the color of the reaction turns to black. The mixture was stirred at room temperature for 30 min and heated at 50° C. overnight under N2. Triethylamine was removed under reduce pressure and the crude product was purified by flash chromatography (Prepacked column 50 g, Cyclohexane/AcOEt: 60/40 as eluent) following by C18 chromatography (Prepacked column 15 g, H2O/CH3CN: from 80/20 to 40/600 as eluent) to afford 120 mg of 2-(4-(3-fluoropyridin-2-yl)but-3-ynyl)benzo[d]oxazole (Yield: 15%) as white powder (Mp=86-88° C.).

Workup

  1. customIn a dry reaction tube
  2. customA yellow suspension was obtained
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. temperatureheated at 50° C. overnight under N2
  5. customTriethylamine was removed
  6. customthe crude product was purified by flash chromatography (Prepacked column 50 g, Cyclohexane/AcOEt: 60/40 as eluent)

Sources & evidence

ORD record
ord-e14e994e76084d638e7cd590dc5ffb89
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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