Tetrahydrofuran → HCID 69673986, compound

HRID 2041874Notes

Reaction equation

HRID 2041874 reaction equation
O1CCCC1.Br[C:7]1[N:8]=[CH:9][S:10][CH:11]=1.[CH2:12]([N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26])[CH2:13][C:14]#[CH:15]>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)I.C(N(CC)CC)C>[S:10]1[CH:11]=[CH:7][N:8]=[C:9]1[C:15]#[C:14][CH2:13][CH2:12][N:16]1[C:20](=[O:21])[C:19]2[C:18](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]1=[O:26]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 27632184-BromothiazoleHCID 11171619N-(3-Butynyl)phthalimide

Product 1

HCID 69673986HCID 69673986, compoundYield 67.5%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, 78 ml of tetrahydrofuran, 5.49 g of 4-bromothiazole, and 20.3 ml of triethylamine were added to 1184 mg of dichlorobis(triphenylphosphine)palladium, 322 mg of copper iodide, and 6.64 g of N-(3-butynyl)phthalimide. The obtained mixture was stirred under reflux for 5 hours. After completion of the stirring, the reaction solution was cooled to a room temperature, and a solid was then filtrated. The filtrate was concentrated, and the residue was then purified by column chromatography (Wako Gel C-200; toluene:ethyl acetate=4:1), so as to obtain 6.35 g of a phthalimide compound.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationa solid was then filtrated
  3. concentrationThe filtrate was concentrated
  4. customthe residue was then purified by column chromatography (Wako Gel C-200; toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-71d8556195ec423a873e96cf777661ab
Source dataset
uspto-grants-2013_11
Patent number
US08586505B2

Reaction notes

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