2-Bromopyridine → 4-(Pyridin-2-yl)but-3-yn-1-ol

HRID 334546Notes

Reaction equation

HRID 334546 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([OH:12])[CH2:9][C:10]#[CH:11]>C(N(CC)CC)C.[Cu+2].[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>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][CH2:8][OH:12]

Participants

6

Reactant 2

HCID 79732-BromopyridineHCID 135663-Butyn-1-OL

Product 1

HCID 110080634-(Pyridin-2-yl)but-3-yn-1-olYield 74.7%

Reagents, catalysts & solvents 3

HCID 44148441CID 44148441CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent2×

Procedure

In a dry reaction tube containing in suspension iodide copper (38 mg, 0.2 mmol) and triethylamine (11 mL, 80 mmol), were added 2-bromopyridine (632 mg, 4 mmol) and Pd(PPh3)2Cl2 (140 mg, 0.2 mmol). A yellow suspension is obtained and after a few minutes of stirring at room temperature, was added a solution of but-3-yn-1-ol (280 mg, 4 mmol) in triethylamine (2.2 mL). Immediately the color of the reaction turns to black. The mixture was stirred at room temperature for 30 min and then at 80° C. for 20 h. Triethylamine was concentrated under reduced pressure and the residue was dissolved in DCM. The organic layer was washed with saturated NH4Cl, water and brine, dried (MgSO4) and concentrated. The product was purified by flash chromatography (prepacked 15 g silicagel column, from DCM 100% to DCM/MeOH: 98/2 as eluent) to afford 440 mg of 4-(pyridin-2-yl)but-3-yn-1-ol (Yield: 74%) as brown oil.

Workup

  1. customIn a dry reaction tube
  2. customA yellow suspension is obtained and after a few minutes
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. concentrationTriethylamine was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in DCM
  6. washThe organic layer was washed with saturated NH4Cl, water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (prepacked 15 g silicagel column, from DCM 100% to DCM/MeOH: 98/2 as eluent)

Sources & evidence

ORD record
ord-4a9667b8fb0d47a98cbc1518e0c63a26
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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