Trimethylsilylacetylene → Thiazole, 2-[(trimethylsilyl)ethynyl]-

HRID 2096201Notes

Reaction equation

HRID 2096201 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([Si:9]([CH3:12])([CH3:11])[CH3:10])#[CH:8]>C1COCC1.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>[CH3:10][Si:9]([CH3:12])([CH3:11])[C:7]#[C:8][C:2]1[S:3][CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 764302-Bromothiazole

Product 1

HCID 11622446Thiazole, 2-[(trimethylsilyl)ethynyl]-

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-Bromothiazole (Aldrich, 5.0 g, 30.5 mmol), ethynyl-trimethyl-silane (Aldrich, 3.0 g, 30.5 mmol), PdCl2(PPh3)2 (Aldrich, 500 mg, 0.71 mmol) and CuI (Aldrich, 400 mg, 1.52 mmol) in THF (20 mL) was treated with TEA (5 mL) at room temperature for 20 min. The reaction was heated at 60 for 4 hours. The solid was filtered off through a pad of celite and the filtrate was concentrated to give yellow solid, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as yellow oil.

Workup

  1. temperatureThe reaction was heated at 60 for 4 hours
  2. filtrationThe solid was filtered off through a pad of celite
  3. concentrationthe filtrate was concentrated
  4. customto give yellow solid, which
  5. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-20281339fc2f4d328092724c2d7da876
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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