Dimethylformamide → 5-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehyde

HRID 1921310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921310
Br[C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.C[C:10]1([CH3:23])[C:15]([CH3:17])(C)[CH:14]=[N:13][C:12](B2OCCO2)=[CH:11]1.[C:24](=[O:27])([O-])[O-].[K+].[K+].CN(C)[CH:32]=[O:33]>O.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]>[CH2:10]([C:15]1[CH:17]=[C:7]([C:5]2[O:6][C:2]([CH:24]=[O:27])=[CH:3][CH:4]=2)[C:12]([CH3:11])=[N:13][C:14]=1[O:33][CH3:32])[CH3:23]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 6003285-Bromofuran-2-carbaldehydeHCID 866103514,4,5,5-Tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine

Produkt 1

HCID 116228885-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehydeAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178478476HCID 178478476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a mixture of 5-bromofuran-2-carbaldehyde (1.25 g, 7.14 mmol), 3-ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine (1.32 g, 4.76 mmol), prepared in accordance with one of the procedures of Step 1, PREPARATION 2, potassium carbonate (2.63 g, 7.14 mmol) and dimethylformamide (30 mL) under a nitrogen atmosphere is added dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium dichloromethane adduct (0.2 g, 6 mol %) and the mixture is stirred at 90° C. for 2 hr. The reaction is cooled, diluted with water and washed with water. The organic layer is separated, dried, filtered and concentrated. The residue is purified by flash chromatography eluting with heptane-30% ethyl acetate to afford 5-(5-ethyl-6-methoxy-2-methylpyridin-3-yl)furan-2-carbaldehyde (1.2 g, 103% yield). MS: m/e=246 (M+H). 1H-NMR (CDCl3, δ ppm) 9.64 (s, 1H), 7.79 (s, 1H), 7.33 (d, 1H, J=3.8 Hz), 6.67 (d, 1H, J=3.8 Hz); 3.99 (s, 3H); 2.64 (s, 3H); 2.61 (q, 2H, J=7.6 Hz), 1.21 (t, 3H, J=7.6 Hz).

Aufarbeitung

  1. temperatureThe reaction is cooled
  2. washwashed with water
  3. customThe organic layer is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography
  8. washeluting with heptane-30% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-73fab38bd5af43fdb36b09473b8065c0
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173682B2

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