2-Bromopyridine → HCID 53685790, compound

HRID 842090Notes

Reaction equation

HRID 842090 reaction equation
Cl[C:2]1[CH:3]=[C:4](C#C)[C:5]2[O:9][C:8]([CH2:10][C:11]3[CH:16]=[C:15](C(C)(C)C)[C:14](O)=[C:13](C(C)(C)C)[CH:12]=3)=[N:7][C:6]=2[CH:26]=1.BrC1C=CC=C[N:31]=1>C(N(CC)CC)C.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.[Cu]I>[N:31]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:11]#[C:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][CH:2]=[CH:26][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 79732-BromopyridineHCID 15521191HCID 15521191, compound

Product 1

HCID 53685790HCID 53685790, compoundYield 224%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 5-chloro-2-(3,5-di-t-butyl-4-hydroxy-benzyl)-7-ethynyl-benzoxazole (2.38 g, 6.0 mmol), 2-bromo-pyridine (0.66 ml, 98%, 6.6 mmol), bis(triphenylphosphine)palladium(II) dichloride (21.1 mg, 30 μmol) and copper (I) iodide (1.2 mg, 6 μmol) in triethylamine (12 ml) was heated at 90° C., under argon, for 1.5 hours. The triethylamine was removed in-vacuo and the residue dissolved in ether (100 ml). The organics were washed with water (50 ml), 1 N HCl (100 ml) and saturated aqueous sodium hydrogen carbonate (100 ml), dried (Na2SO4) and evaporated in-vacuo to give 2.96 g (104.2%) of crude pyridylethynylbenzoxazole. The crude benzoxazole was purified by column chromatography (SiO2; dichloromethane), and the product crystallized from methanol and suspended in hot water. The resulting crystals were collected, washed, and dried to give 1.49 g (52.5%) of the title compound (mp 138-9° C.).

Workup

  1. customThe triethylamine was removed in-vacuo
  2. dissolutionthe residue dissolved in ether (100 ml)
  3. washThe organics were washed with water (50 ml), 1 N HCl (100 ml) and saturated aqueous sodium hydrogen carbonate (100 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in-vacuo

Sources & evidence

ORD record
ord-da91b47bab8c44b6a132ebf34751e61d
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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