Toluene → Ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate

HRID 592130

Reaktionsgleichung

Reaktionsgleichung von HRID 592130
[CH3:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][N:3]=1.I[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 14974990Ethyl (4-iodophenyl)acetateHCID 164142742-Methylpyridine-4-boronic acid pinacol ester

Produkt 1

HCID 58447956Ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a sealed tube were added 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.2 g, 10 mmol), ethyl 2-(4-iodophenyl)acetate 26-1 (2.9 g, 10 mmol), Pd(PPh3)4 (0.231 g, 0.2 mmol), toluene (30 mL), ethanol (10 mL) and 2M Na2CO3 (10 mL). The reaction mixture was flushed with nitrogen and stirred at 90° C. for 10 hours. After cooled down to room temperature, the reaction mixture was diluted into 200 mL ethyl acetate and washed with saturated sodium bicarbonate solution and then brine. The organic phase was dried over Na2SO4 and then taken to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate 26-2 as an oil. MS m/z 256.1 (M+1).

Aufarbeitung

  1. customThe reaction mixture was flushed with nitrogen
  2. temperatureAfter cooled down to room temperature
  3. additionthe reaction mixture was diluted into 200 mL ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customtaken to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-12ecdbc9d793437094f0f3e0fb79a32f
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238646B2

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