Water → 4-Ethoxycarbonyl-5-(2-trimethylsilylethynyl)thiazole

HRID 2246100Notes

Reaction equation

HRID 2246100 reaction equation
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])#[CH:20].O>CN(C=O)C.[Cu]I.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.CCCCCC.C(OCC)(=O)C>[CH2:10]([O:9][C:7]([C:3]1[N:4]=[CH:5][S:6][C:2]=1[C:20]#[C:19][Si:21]([CH3:24])([CH3:23])[CH3:22])=[O:8])[CH3:11]

Participants

10

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 12361218Ethyl 5-bromo-1,3-thiazole-4-carboxylate

Product 1

HCID 592179544-Ethoxycarbonyl-5-(2-trimethylsilylethynyl)thiazole

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

5-Bromo-4-ethoxycarbonylthiazole (18.64 g) was dissolved in 80 ml of DMF. Triethylamine (22 ml), 16.7 ml of ethynyltrimethylsilane, 960 mg of copper(I) iodide, and 1.11 g of bis(triphenylphosphine)palladium(II) dichloride were added in that order to the solution, and the mixture was stirred at 90° C. under an argon atmosphere for one hr. Water (80 ml), 160 ml of ethyl acetate and 160 ml of hexane were added to the reaction solution, and the mixture was washed with (brine+aqueous hydrochloric acid), sodium bicarbonate water, and brine in that order. Activated carbon and anhydrous magnesium sulfate were added to the organic layer, and the mixture was filtered and was concentrated under the reduced pressure to give 16.45 g of the title compound.

Workup

  1. washthe mixture was washed with (brine+aqueous hydrochloric acid), sodium bicarbonate water, and brine in that order
  2. additionActivated carbon and anhydrous magnesium sulfate were added to the organic layer
  3. filtrationthe mixture was filtered
  4. concentrationwas concentrated under the reduced pressure

Sources & evidence

ORD record
ord-112f5d87068a403aa2d891a00d87b00b
Source dataset
uspto-grants-2010_03
Patent number
US07687490B2

Reaction notes

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