Phenylboronic Acid → 2-acetamido-N-((5-phenyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isonicotinamide

HRID 623660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623660
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][N:27]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[C:16](Br)[CH:17]=1)=[O:9])(=[O:3])[CH3:2].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>O1CCOCC1.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:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][N:27]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[C:16]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:17]=1)=[O:9])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 675096872-acetamido-N-((5-bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isonicotinamide

Produkt 1

HCID 675083942-acetamido-N-((5-phenyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isonicotinamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-acetamido-N-((5-bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isonicotinamide (20 mg, 0.05 mmol, Step-1), phenylboronic acid (11 mg, 0.09 mmol), tetrakis(triphenylphosphine)palladium (3 mg, 2.2 microM) in dioxane (2 mL) is added saturated aqueous sodium hydrogencarbonate (0.4 mL). The mixture is heated at 100° C. for 1 hr. After cooled to room temperature, the mixture is extracted with ethyl acetate, dried over sodium sulfate. The organic solvent is removed under reduced pressure. The residue is purified by short column chromatography on amine gel eluting with ethylacetate, and then purified by preparative LC-MS to give 6 mg (30% yield) of the title compound.

Aufarbeitung

  1. temperatureAfter cooled to room temperature
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe organic solvent is removed under reduced pressure
  5. customThe residue is purified by short column chromatography on amine gel
  6. washeluting with ethylacetate
  7. custompurified by preparative LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-e3a7e2a9a0f6446e9be6940130e82e8f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302991B2

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