Tributylvinyltin → 2-Methylamino-5-vinyl-nicotinic acid ethyl ester

HRID 2244354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244354
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9](Br)[CH:8]=[N:7][C:6]=1[NH:12][CH3:13])[CH3:2].[Cl-].[Li+].[CH:17]([Sn](CCCC)(CCCC)CCCC)=[CH2:18]>CS(C)=O.[Cu]Cl.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>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([CH:17]=[CH2:18])[CH:8]=[N:7][C:6]=1[NH:12][CH3:13])[CH3:2]

Komponenten

7

Edukt 3

HCID 81998Tributylvinyltin2×HCID 433294Lithium ChlorideHCID 687024045-Bromo-2-methylamino-nicotinic acid ethyl ester

Produkt 1

HCID 686973712-Methylamino-5-vinyl-nicotinic acid ethyl esterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 62652Cuprous chlorideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-2-methylamino-nicotinic acid ethyl ester (100 mg, 0.39 mmol), lithium chloride (98 mg, 2.32 mmol), copper(I)chloride (191 mg, 1.93 mmol), vinyl tributyl tin (151 mg, 0.46 mmol), and tetrakis(triphenylphosphine)palladium(0) (45 mg, 39 μmol) in methyl sulfoxide (3.1 mL) was stirred at 65° C., then after 4 h another portion of vinyl tributyl tin (141 mg, 0.46 mmol) was added, and stirring was continued for 18 h. After cooling, the reaction mixture was partitioned between sat. aq. ammonium chloride solution and diethyl ether, the organic layer was washed with water, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (72 mg, 91%). Yellow liquid, MS (ISP): 207.1 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between sat. aq. ammonium chloride solution and diethyl ether
  3. washthe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4cf46e7d474e49d5a06558f9b773212e
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678818B2

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