Tetrahydrofuran → HCID 69673475, compound

HRID 2041870Notes

Reaction equation

HRID 2041870 reaction equation
O1CCCC1.[C:6]1([C:12]2[S:13][CH:14]=[C:15](Br)[N:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]([N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])[CH2:19][C:20]#[CH:21]>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>[C:6]1([C:12]2[S:13][CH:14]=[C:15]([C:21]#[C:20][CH2:19][CH2:18][N:22]3[C:26](=[O:27])[C:25]4[C:24](=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:23]3=[O:32])[N:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 11171619N-(3-Butynyl)phthalimideHCID 118315284-broMo-2-phenylthiazole

Product 1

HCID 69673475HCID 69673475, compoundYield 55.6%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, 15 ml of tetrahydrofuran, 1.50 g of the 2-phenyl-4-bromothiazole obtained in the above described stage, and 3.8 ml of triethylamine were added to 221 mg of dichlorobis(triphenylphosphine)palladium, 60 mg of copper iodide, and 1.24 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 1.24 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-dc51c24b68d347fba5055ed5ad1f1a54
Source dataset
uspto-grants-2013_11
Patent number
US08586505B2

Reaction notes

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