2-Bromothiazole → HCID 20071656, compound

HRID 981052Notes

Reaction equation

HRID 981052 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][N:8]([CH3:12])[CH2:9][C:10]#[CH:11]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[CH3:7][N:8]([CH3:12])[CH2:9][C:10]#[C:11][C:2]1[S:3][CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 2

HCID 764302-BromothiazoleHCID 81643N,N-Dimethylpropargylamine

Product 1

HCID 20071656HCID 20071656, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 5.02 g of 2-bromothiazole, 20 ml of triethylamine, and 4.3 ml of 1-dimethylamino-2-propyne is stirred under argon for 5 minutes. Seven hundred and fifty milligrams of bis(triphenylphosphine) palladium (II) chloride and 0.450 mg of copper (I) iodide is added and the stirred reaction is heated at 80°-85° C. for 3 hours. The reaction mixture is cooled, partitioned between diethyl ether and 65 ml of 10% sodium carbonate, and the layers are separated. The organic layer is filtered through diatomaceous earth, washed with aqueous sodium chloride and dried over magnesium sulfate. The crude product is purified by chromatography using silica gel as absorbant followed by filtration of the product band through a pad of magnesium silicate to give 0.35 g of the desired product as an oil, MH+ 167. Purity is determined by 1H PMR spectroscopy and by thin layer chromatography.

Workup

  1. customthe stirred reaction
  2. temperatureis heated at 80°-85° C. for 3 hours
  3. temperatureThe reaction mixture is cooled
  4. custompartitioned between diethyl ether and 65 ml of 10% sodium carbonate
  5. customthe layers are separated
  6. filtrationThe organic layer is filtered through diatomaceous earth
  7. washwashed with aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customThe crude product is purified by chromatography
  10. filtrationas absorbant followed by filtration of the product band through a pad of magnesium silicate

Sources & evidence

ORD record
ord-ab5bee9349fa4692880f8f6943fd3e25
Source dataset
uspto-grants-1991_02
Patent number
US04990520

Reaction notes

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