Tetrahydrofuran → HCID 69673265, compound

HRID 2041872Notes

Reaction equation

HRID 2041872 reaction equation
O1CCCC1.[CH2:6]([C:13]1[S:14][CH:15]=[C:16](Br)[N:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:19]([N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])[CH2:20][C:21]#[CH:22]>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>[CH2:6]([C:13]1[S:14][CH:15]=[C:16]([C:22]#[C:21][CH2:20][CH2:19][N:23]2[C:27](=[O:28])[C:26]3[C:25](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24]2=[O:33])[N:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 11171619N-(3-Butynyl)phthalimideHCID 69674030HCID 69674030, compound

Product 1

HCID 69673265HCID 69673265, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, 9 ml of tetrahydrofuran, 1.02 g of the 2-benzyl-4-bromothiazole obtained in the above described stage, and 2.3 ml of triethylamine were added to 143 mg of dichlorobis(triphenylphosphine)palladium, 38 mg of copper iodide, and 0.80 g of N-(3-butynyl)phthalimide. The obtained mixture was stirred under reflux for 4 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=9:1), so as to obtain 1.00 g of a phthalimide compound.

Workup

  1. temperatureunder reflux for 4 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=9:1)

Sources & evidence

ORD record
ord-ee8b7bc580da4fb0ade86fecaa005026
Source dataset
uspto-grants-2013_11
Patent number
US08586505B2

Reaction notes

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