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Water → N-[4-(6-Amino-2'-methyl-3,4'-bipyridin-5-yl)phenyl]-1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide

HRID 1428120
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1428120
O.C(=O)([O-])[O-].[K+].[K+].[NH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[C:29](=[O:30])[C:28]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)=[CH:27][N:26]([CH2:38][CH2:39][F:40])[CH:25]=3)=[O:23])=[CH:17][CH:16]=2)=[CH:13][C:12](Br)=[CH:11][N:10]=1.[CH3:42][C:43]1[CH:48]=[C:47](B2OC(C)(C)C(C)(C)O2)[CH:46]=[CH:45][N:44]=1>O1CCOCC1.C(Cl)(Cl)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>[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:47]2[CH:46]=[CH:45][N:44]=[C:43]([CH3:42])[CH:48]=2)=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[C:29](=[O:30])[C:28]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[CH:27][N:26]([CH2:38][CH2:39][F:40])[CH:25]=2)=[O:23])=[CH:17][CH:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 86700059N-[4-(2-Amino-5-bromopyridin-3-yl)phenyl]-1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide

Produkt 1

HCID 86700074
N-[4-(6-Amino-2'-methyl-3,4'-bipyridin-5-yl)phenyl]-1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide
Ausbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6212ChloroformLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Water (0.1 ml), potassium carbonate (48 mg) and tetrakis(triphenylphosphine)palladium (13 mg) were added to a solution of the compound obtained in Step 1 of Example 43 (61 mg) and 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (28 mg) in 1,4-dioxane (1.2 ml), and the mixture was stirred at 100° C. for six hours. After leaving to cool, the reaction solution was diluted with chloroform. The organic layer was washed with water and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->10:1 (v/v)] to give 24 mg of the title compound as a solid.

Aufarbeitung

  1. customAfter leaving
  2. temperatureto cool
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->10:1 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-14b6dafa556c4761aa966e9ca47ef508
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08933103B2

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