Toluene → 5-(Pyridin-3-yl)thiophene-2-carbaldehyde

HRID 1421536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421536
Br[C:2]1[S:6][C:5]([CH2:7][OH:8])=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:10]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 11435467(5-Bromothiophen-2-yl)methanol

Produkt 1

HCID 108994275-(Pyridin-3-yl)thiophene-2-carbaldehydeAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 153 mg (5-bromo-thiophen-2-yl)-methanol, 128 mg pyridine-3-boronic acid, and 64 mg tetrakis(triphenylphosphine) palladium was added solvent (7.3 mL toluene and 3.1 mL methanol) followed by 1.4 mL of 2.5M sodium carbonate and the mixture heated to 80° C. on an oil bath. After 16 hours the mixture was cooled to room temperature and cocncentrated in vacuo. The residue was solvated in ethyl acetate was washed sequentially with 0.5N sodium hydroxide and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane:ethyl acetate, 60:40; then 55:45) gave the title compound (147 mg).

Aufarbeitung

  1. temperatureAfter 16 hours the mixture was cooled to room temperature
  2. washwas washed sequentially with 0.5N sodium hydroxide and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (hexane

Quellen und Nachweise

ORD-Eintrag
ord-6d1d548fb35c4ea4a84adebc3912f6e5
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077858

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