Triethylamine → HCID 86618274, compound

HRID 1443638Notes

Reaction equation

HRID 1443638 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)#[CH:2].Br[C:12]1[S:13][CH:14]=[CH:15][N:16]=1.C(N(CC)CC)C>C(#N)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>[S:13]1[CH:14]=[CH:15][N:16]=[C:12]1[C:8]1[CH:7]=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:1]#[CH:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 764302-BromothiazoleHCID 2510201-Ethynyl-4-methoxybenzene

Product 1

HCID 86618274HCID 86618274, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

The alkyne of the current example, 2-(2-thiazolyl)-4-methoxyphenylacetylene was prepared by adding to a degassed solution of 4 mmol of 4-ethynylanisole, 4 mmol of 2-bromothiazole, and 1 ml of triethylamine in 10 ml of acetonitrile, 140 mg (0.2 mmol) of PdCl2(PPh3)2 and 19 mg(0.1 mmol) of CuI. The mixture was degassed and stirred for 5 minutes at RT and heated to 90° C. for 12 hours. The reaction mixture was concentrated in vacuo and purified by silica column to afford 0.61 g of brown liquid in a 70% yield.

Workup

  1. customThe mixture was degassed
  2. temperatureheated to 90° C. for 12 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by silica column

Sources & evidence

ORD record
ord-035a3f6ce93f48e080c7dfa84172e037
Source dataset
uspto-grants-2010_02
Patent number
US07662779B2

Reaction notes

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