2-Bromopyridine → HCID 53685790, compound

HRID 1377540Notes

Reaction equation

HRID 1377540 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 104.2%

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 mM), 2-bromo-pyridine (0.66 ml, 98%, 6.6 mM), bis(triphenylphosphine)palladium(II) dichloride (21.1 mg, 30 uM) and copper (I) iodide (1.2 mg, 6 uM) 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), 1N 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 (top 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), 1N 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-217b1334110e427cbbf19573676f7a2d
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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