2-Bromothiazole → HCID 22618309, compound

HRID 1377541Notes

Reaction equation

HRID 1377541 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(C(C)(C)C)C(O)=C(C(C)(C)C)C=3)=[N:7][C:6]=2[CH:26]=1.BrC1[S:31][CH:32]=[CH:33][N:34]=1>C(N(CC)CC)C.[Pd](Cl)Cl.[Cu]I>[S:31]1[CH:32]=[CH:33][N:34]=[C:16]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 764302-BromothiazoleHCID 15521191HCID 15521191, compound

Product 1

HCID 22618309HCID 22618309, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 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-bromothiazole (1.13 ml, 95%, 12 mM), bistriphenylphosphine)palladium(II) dichloride (21.1 mg, 30 uM), copper (I) iodide (1.2 mg, 6 uM) in triethylamine (12 ml) was heated at 90° C., under argon, for 3 hours. The triethylamine was removed in-vacuo and the residue dissolved in ether (70 ml) and water (30 ml). The organics were washed with 1N HCl (30 ml) and saturated sodium hydrogen carbonate (30 ml), dried (Na2SO4) and evaporated in-vacuo to give 2.86 g (100%) of crude thiazolylethynylbenzoxazole, which was purified by flash chromatography (SiO2 ; dichloromethane). The product was crystallized and recrystallized from methanol to give 1.43 g (50.4%) of the title compound (mp 137°-41° C.).

Workup

  1. customThe triethylamine was removed in-vacuo
  2. dissolutionthe residue dissolved in ether (70 ml)
  3. washThe organics were washed with 1N HCl (30 ml) and saturated sodium hydrogen carbonate (30 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in-vacuo

Sources & evidence

ORD record
ord-50dcce7feb18421e8dd03b68c7a20197
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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