3-Bromopyridine → 5-(3-Pyridinyl)-4-pentyn-1-ol

HRID 2403833Notes

Reaction equation

HRID 2403833 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([OH:13])[CH2:9][CH2:10][C:11]#[CH:12]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:12]#[C:11][CH2:10][CH2:9][CH2:8][OH:13])[CH:3]=1

Participants

6

Reactant 2

HCID 122863-BromopyridineHCID 793464-Pentyn-1-ol

Product 1

HCID 107970615-(3-Pyridinyl)-4-pentyn-1-ol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

3-Bromopyridine (5.4 g, 34.2 mmol) was dissolved in triethylamine (10 ml) and degassed under nitrogen. 4-Pentyn-1-ol (3.50 ml, 37.6 mmol) was added followed by bis(triphenylphosphine)palladium (II) chloride (0.245 g, 0.349 mmol) and copper(I)iodide (0.136 g, 0.714 mmol) and the resulting mixture was stirred and heated under reflux for 20 mins. when a dark brown sludge was obtained. The mixture was cooled to rt and partitioned between EtOAc (200 ml) and water (50 ml).

Workup

  1. customdegassed under nitrogen
  2. temperatureheated
  3. temperatureunder reflux for 20 mins
  4. customwhen a dark brown sludge was obtained
  5. custompartitioned between EtOAc (200 ml) and water (50 ml)

Sources & evidence

ORD record
ord-5f75e3fd1aa54912af11b2f0fa5ff95b
Source dataset
uspto-grants-2014_08
Patent number
US08802684B2

Reaction notes

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