Sodium Carbonate → 2-Fluoro-4-[7-(1-quinolin-6-ylethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzonitrile

HRID 500242Notizen

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([CH:17]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)[CH3:18])=[CH:15][N:16]=3)[N:13]=2)=[CH:4][C:3]=1[F:29].C(=O)([O-])[O-].[Na+].[Na+].[CH3:36][N:37](C)C(=O)C>CCOC(C)=O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.O.O.O.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:29][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([CH:17]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)[CH3:18])=[CH:15][N:16]=3)[N:13]=2)[CH:6]=[CH:7][C:2]=1[C:36]#[N:37]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 6-1-[2-(4-bromo-3-fluorophenyl)imidazo[1,2-b][1,2,4]triazin-7-yl]ethylquinoline (0.100 g, 0.223 mmol), potassium hexacyanoferrate(II) trihydrate (30 mg, 0.06 mmol), sodium carbonate (0.047 g, 0.45 mmol) and palladium acetate (2 mg, 0.01 mmol) in N,N-dimethylacetamide (1.2 mL) was stirred at 120° C. for 2 h. LCMS showed the reaction was complete. The reaction was diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography on silica gel with MeOH in methylene chloride (0-10%) to afford the desired product (0.10 g, 60%). LCMS: (M+H)=395.0.

Aufarbeitung

washwashed with water, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel with MeOH in methylene chloride (0-10%)

Quellen und Nachweise

ORD-Eintrag: ord-b8d3400d2b984ca4a00bf82fa8280be6
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07767675B2

Notizen zur Reaktion

Wird geladen…