Triethylamine → HCID 58227511, compound

HRID 2092962Notes

Reaction equation

HRID 2092962 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=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.O1CCCC1>[CH2:18]([O:17][C:15]([C:12]1[S:11][C:10]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:14][CH:13]=1)=[O:16])[CH3:19]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 58227511HCID 58227511, compoundYield 73%

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 phenylacetylene (6.15 ml, 55.9 mmol), ethyl 2-bromothiazole-5-carboxylate (7.59 ml, 50.8 mmol), bis(triphenylphosphine)palladium(II) chloride (1.07 g, 1.52 mmol), copper (I) iodide (581 mg, 3.05 mmol), triethylamine (100 ml, 717 mmol) and tetrahydrofuran (225 mL) was stirred at 25° C. for 16 h. The reaction was worked up by concentrating to remove the THF and taken up in 400 mL of CHCl3. The CHCl3 was washed with 2×75 mL of 3.7% aq. HCl, 75 mL of brine, and dried (Na2SO4). The material was purified by silica gel chromatography using a gradient elution going from 4.5% to 8.5% EtOAc in hexanes over 30 minutes to give the titled compound, 2-phenylethynyl-thiazole-5-carboxylic acid ethyl ester (9.5 g, 73% yield), as a solid, which was used without further purification in the next step.

Workup

  1. concentrationby concentrating
  2. customto remove the THF
  3. washThe CHCl3 was washed with 2×75 mL of 3.7% aq. HCl, 75 mL of brine
  4. dry with materialdried (Na2SO4)
  5. customThe material was purified by silica gel chromatography
  6. washa gradient elution

Sources & evidence

ORD record
ord-6ebd4405e5a84461874fe8465d7045a4
Source dataset
uspto-grants-2013_05
Patent number
US08440837B2

Reaction notes

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