Triethylamine → 4-(4-Nitro-2-(trifluoromethyl)phenylethynyl)pyridine

HRID 1912882

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)#[CH:16].C(N(CC)CC)C>CN(C)C=O.[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>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:16]#[C:15][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

In 20 mL of dimethylformamide, 1.0 g (3.7 mmol) of 4-bromo-3-(trifluoromethyl)nitrobenzene was dissolved, and 0.502 g (3.7 mmol) of 4-ethynylpyridine, 43 mg (3 mol %) of copper iodide, 78 mg (3 mol %) of dichlorobis(triphenylphosphine)palladium and 2.06 mL (0.56 mmol) of triethylamine were added thereto and the mixture solution was stirred overnight at 50° C. in an argon atmosphere. The reaction solution was partitioned between water and ethyl acetate and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The residue was purified by a silica gel column (n-hexane:ethyl acetate=3:1) to obtain 1.3 g (quantitative) of a target product as an pale yellow oil.

Aufarbeitung

customThe reaction solution was partitioned between water and ethyl acetate
washthe organic layer was washed with a saturated sodium chloride solution
concentrationconcentrated under reduced pressure
customThe residue was purified by a silica gel column (n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag: ord-178350c2f3cf4c4ebf09de628cdceeb6
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08609656B2

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