Hydrochloric Acid → HCID 68008364, Verbindung

HRID 533161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533161
Br[C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC.Cl.C(=O)(O)[O-].[Na+].[C:34]1(C)C=CC=C[CH:35]=1>C1(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)C=CC=CC=1>[CH:13]([C:5]1[N:4]=[CH:3][C:2]([CH:34]=[CH2:35])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])=[CH2:14]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 81998TributylvinyltinHCID 516892Sodium BicarbonateHCID 2763343Methyl 5-bromo-2-chloronicotinate

Produkt 1

HCID 68008364HCID 68008364, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178420554HCID 178420554, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Methyl 5-bromo-2-chloronicotinate (6.9 g, 27.6 mmol) was dissolved into toluene (100 mL). Tributyl(vinyl)tin (19.7 g, 62.1 mmol) was added, followed by tetrakistriphenylphosphinopalladium (2.5 g, 2.1 mmol), and the reaction heated at 110° C. for 3 h. The reaction mixture was poured onto 2 N HCl (100 mL) and stirred for 30 min, then neutralized with saturated sodium bicarbonate. The organic layer was removed, concentrated and purified over silica gel using automated chromatography to give 4.5 g (86%) of the compound. LC-MS (M+H)=190.1.

Aufarbeitung

  1. customThe organic layer was removed
  2. concentrationconcentrated
  3. custompurified over silica gel using automated chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f821f7e0e89d4d5bbf7211364d9b9990
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853237B2

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