Potassium Carbonate → N-((2'-fluoro-[2,4'-bipyridin]-5-yl)methyl)-2-oxo-2H-[1,3'-bipyridine]-6'-carboxamide

HRID 711250Notizen

Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([F:24])[CH:19]=3)=[N:16][CH:17]=2)=[O:9])=[N:6][CH:7]=1.[OH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[F:24][C:20]1[CH:19]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][NH:10][C:8]([C:5]3[N:6]=[CH:7][C:2]([N:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]4=[O:25])=[CH:3][CH:4]=3)=[O:9])=[CH:17][N:16]=2)[CH:23]=[CH:22][N:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 108 °C

Versuchsvorschrift

A mixture of 5-bromo-N-42′-fluoro-[2,4′-bipyridin]-5-yl)methyl)picolinamide 38-4 (38.6 mg, 0.1 mmol), 2-hydroxypyridine 44-1 (19.0 mg, 0.2 mmol), CuI (9.5 mg, 0.05 mmol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (7.1 mg, 0.05 mmol) and K2CO3 (28 mg, 0.20 mmol) in toluene (0.6 mL) was stirred at 108° C. for 8 hours. After cooling to room temperature, the mixture was filtered through celite (washed with ethyl acetate) and the filtrate was concentrated with rotavap. The residue was subjected to preparative reverse phase HPLC separation to give N-42′-fluoro-[2,4′-bipyridin]-5-yl)methyl)-2-oxo-2H-[1,3′-bipyridine]-6′-carboxamide 44 as a solid.

Aufarbeitung

temperatureAfter cooling to room temperature
filtrationthe mixture was filtered through celite (washed with ethyl acetate)
concentrationthe filtrate was concentrated with rotavap
customThe residue was subjected to preparative reverse phase HPLC separation

Quellen und Nachweise

ORD-Eintrag: ord-4175095b8e60402083459e4fcc7226c9
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09181235B2

Notizen zur Reaktion

Wird geladen…