3,5-Dibromopyridine → 3-Bromo-5-(3-fluorophenylethynyl)-pyridine

HRID 606869Notes

Reaction equation

HRID 606869 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1)#[CH:2].[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15](Br)[CH:16]=1>C(N(CC)CC)C.C(OCC)(=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=2)[CH:16]=1

Participants

7

Reactant 2

HCID 693693,5-DibromopyridineHCID 5202181-Ethynyl-3-fluorobenzene

Product 1

HCID 670478123-Bromo-5-(3-fluorophenylethynyl)-pyridineYield 28%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Add 1-ethynyl-3-fluorobenzene (250 mg, 2.11 mmol) to a mixture of 3,5-dibromopyridine (500 mg, 2.11 mmol) in triethylamine (4 mL) containing bis(triphenylphosphine)palladium (II) dichloride (28 mg, 0.04 mmol) and copper (I) iodide (15 mg, 0.08 mmol) and heat at 70° C. for 2 h. Cool to room temperature, dilute with ethyl acetate and an aqueous solution of ammonium chloride and separate the resulting layers. Wash the organic layer with an aqueous saturated solution of sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 0.5% ethanol in 50:50 dichloromethane:hexanes to give the title compound (160 mg, 28%).

Workup

  1. temperatureCool to room temperature
  2. customan aqueous solution of ammonium chloride and separate the resulting layers
  3. washWash the organic layer with an aqueous saturated solution of sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by silica gel chromatography
  8. washeluting with 0.5% ethanol in 50:50 dichloromethane

Sources & evidence

ORD record
ord-21f19bd6ddf0426aaac12d96e8c85643
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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