Tetrahydrofuran → HCID 69673475, compound

HRID 1527613Notes

Reaction equation

HRID 1527613 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.[C:21]1([C:27]2[S:28][CH:29]=[C:30](Br)[N:31]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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>[C:21]1([C:27]2[S:28][CH:29]=[C:30]([C:4]#[C:3][CH2:2][CH2:1][N:5]3[C:9](=[O:10])[C:8]4[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:6]3=[O:15])[N:31]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=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

To 221 mg of dichlorobis(triphenylphosphine)palladium, 60 mg of copper iodide, and 1.24 g of N-(3-butynyl)phthalimide were added 15 ml of tetrahydrofuran, 1.50 g of the 2-phenyl-4-bromothiazole obtained in the foregoing stage, and 3.8 ml of triethylamine in a nitrogen atmosphere, and the mixture was stirred under reflux for 4 hours. After the stifling, 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=9:1) to give 1.24 g of a phthalimide compound.

Workup

  1. temperatureunder reflux for 4 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=9:1)

Sources & evidence

ORD record
ord-3145085443a94fa186d80d27f3432910
Source dataset
uspto-grants-2015_07
Patent number
US09089139B2

Reaction notes

Loading…