Heptane → HCID 11673096, Verbindung

HRID 1921379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921379
CC1(C)C(C)(C)C=[N:5][C:4](B2OCCO2)=C1.[C:16](=[O:19])([O-])[O-].[K+].[K+].Br[C:23]1[S:24][CH:25]=[CH:26][CH:27]=1.[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)C=O.C(OCC)(=O)C.ClCCl.[Pd].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:29]([C:30]1[C:4]([O:19][CH3:16])=[N:5][C:33]([CH3:34])=[C:32]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH:31]=1)[CH3:28]

Komponenten

8

Edukt 4

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 138512-BromothiopheneHCID 866103514,4,5,5-Tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine

Produkt 1

HCID 11673096HCID 11673096, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178478476HCID 178478476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
107.5 °C

Versuchsvorschrift

Under a nitrogen atmosphere, a three neck round bottom flask is charged with 3-ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine (7.8 g, 28.14 mmol) as prepared above, potassium carbonate (9.72 g, 70.33 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium dichloromethane (1.23 mg, 1.68 mmol) followed by anhyd dimethylformamide (100 mL). To this is added a solution of 2-bromothiophene (9.2 g, 56.44 mmol) in dimethylformamide (10 mL) and the resulting mixture is heated to 105-110° C. for 16 hr. The reaction is cooled, diluted with ethyl acetate and washed with water, with brine, dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography eluting with heptane, then heptane-5% ethyl acetate to afford 3-ethyl-2-methoxy-6-methyl-5-(thiophen-2-yl)pyridine as a yellow oil (94% yield).

Aufarbeitung

  1. temperatureThe reaction is cooled
  2. washwashed with water, with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography
  7. washeluting with heptane

Quellen und Nachweise

ORD-Eintrag
ord-b82d2388aee24862b1c66dc077e0cfd6
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173682B2

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