Diethyl Ether → t-butyl N-(2-fluoro-6-cinnamylbenzyl)carbamate

HRID 2390044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390044
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13](I)[C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(O[CH2:22][CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=O)C.C(OCC)C>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 76603-Phenyl-2-propen-1-yl acetateHCID 59323180t-butyl N-(2-fluoro-6-iodobenzyl)carbamate

Produkt 1

HCID 68521872t-butyl N-(2-fluoro-6-cinnamylbenzyl)carbamateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Under an argon atmosphere, 300 mg of t-butyl N-(2-fluoro-6-iodobenzyl)carbamate, 0.29 mL of cinnamyl acetate, 1.28 mL of bistributyltin, and 70 mg of PdCl2(dppf)2 were dissolved in 2.5 mL of DMF, followed by stirring at 120° C. for 2 hours. After completion of the reaction, to the reaction liquid was added diethyl ether, followed by filtration through Celite, and to the filtrate was added water, followed by extraction with diethyl ether. Then, the organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (n-hexane:ethyl acetate=3:1) to obtain 121 mg (yield 52%) of a title compound as a yellow solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customto the reaction liquid
  3. filtrationfollowed by filtration through Celite
  4. additionto the filtrate was added water
  5. extractionfollowed by extraction with diethyl ether
  6. washThen, the organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained
  10. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-4268909112f244f291f124e1d3b18aa5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273766B2

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