Tetrahydrofuran → HCID 69673986, compound

HRID 1527616Notes

Reaction equation

HRID 1527616 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15])[CH2:2][C:3]#[CH:4].O1CCCC1.Br[C:22]1[N:23]=[CH:24][S:25][CH:26]=1>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:25]1[CH:26]=[CH:22][N:23]=[C:24]1[C:4]#[C:3][CH2:2][CH2:1][N:5]1[C:9](=[O:10])[C:8]2[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]1=[O:15]

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

To 1184 mg of dichlorobis(triphenylphosphine)palladium, 322 mg of copper iodide, and 6.64 g of N-(3-butynyl)phthalimide were added 78 ml of tetrahydrofuran, 5.49 g of 4-bromothiazole, and 20.3 ml of triethylamine in a nitrogen atmosphere, and the mixture was stirred under reflux for 5 hours. After the stirring, the reaction mixture was cooled to room temperature and the solids were filtered. After concentrating the filtrate, the residue was purified by column chromatography (Wakogel C-200; toluene:ethyl acetate=4:1) to give 6.35 g of a phthalimide compound.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationthe solids were filtered
  3. concentrationAfter concentrating the filtrate
  4. customthe residue was purified by column chromatography (Wakogel C-200; toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a917f5b2666940d68c252119aa489f10
Source dataset
uspto-grants-2015_07
Patent number
US09089139B2

Reaction notes

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