Ethyl 2-bromo-1,3-thiazole-4-carboxylate → Ethyl 2-(3,4,5-trimethoxyphenylethynyl)thiazole-4-carboxylate

HRID 992999Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[CH:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Br[C:16]1[S:17][CH:18]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:20]=1>CN(C=O)C.C(N(CC)CC)C.C(OCC)(=O)C.[Cu](I)I.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>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]#[C:14][C:16]2[S:17][CH:18]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:20]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 45 °C

Procedure

3,4,5-Trimethoxyphenylacetylene (1.34 g), ethyl 2-bromothiazole-4-carboxylate (1.98 g) and copper iodide (53 mg) were dissolved in a mixed solvent of DMF (3 mL) and triethylamine (6 mL), and to the solution dichlorobis-(triphenylphosphine)palladium (II) (99 mg) was added, and the mixture was stirred at 45° C. for 4 hours under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate. After concentrating the reaction mixture under reduced pressure, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 to 3:1) to obtain the title compound.

Workup

washwashed with 2 M hydrochloric acid, water and saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationAfter concentrating the reaction mixture under reduced pressure
customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 to 3:1)

Sources & evidence

ORD record: ord-dfeb0ab814d249d2b618dd078e8f64e2
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472386B1

Reaction notes

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