Dimethylformamide → 6-((5-(3,5-Difluorophenyl)isoxazolo[5,4-b]pyridin-3-yl)difluoromethyl)quinoline

HRID 40337

Reaktionsgleichung

C(=O)([O-])[O-].[Cs+].[Cs+].ClC1N=[C:12]([C:14](=[N:28][OH:29])[C:15]([F:27])([F:26])[C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[CH:21][CH:20]=[CH:19]3)[C:11](F)=[CH:10][CH:9]=1.[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[C:36]([F:38])[CH:37]=1.[CH3:42][N:43](C=O)C>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[F:31][C:32]1[CH:33]=[C:34]([C:10]2[CH:11]=[C:12]3[C:14]([C:15]([F:26])([F:27])[C:16]4[CH:17]=[C:18]5[C:23](=[CH:24][CH:25]=4)[N:22]=[CH:21][CH:20]=[CH:19]5)=[N:28][O:29][C:42]3=[N:43][CH:9]=2)[CH:35]=[C:36]([F:38])[CH:37]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a pressure vessel was added cesium carbonate (0.61 g, 1.9 mmol), PdCl2(dppf)-CH2Cl2 adduct (26 mg, 0.031 mmol), 1-(6-chloro-3-fluoropyridin-2-yl)-2,2-difluoro-2-(quinolin-6-yl)ethanone oxime (0.26 g, 0.63 mmol) and 3,5-difluorophenylboronic acid (0.15 g, 0.94 mmol) in anhydrous DMF (5 mL) and water (1 mL). The mixture flushed with argon, sealed and stirred at 80° C. for one hour. The suspension was concentrated, triturated with water and filtered to afford a tan solid, purification by MPLC (eluted with a gradient of 20 to 50% ethyl acetate in hexanes) afforded the product as a white solid (23 mg, 9%). MS m/z=410.0 [M+1]+ Calc'd for C22H11F4N3O: 409.3.

Aufarbeitung

customThe mixture flushed with argon
customsealed
concentrationThe suspension was concentrated
customtriturated with water
filtrationfiltered
customto afford
customa tan solid, purification by MPLC (
washeluted with a gradient of 20 to 50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-e06e1bb530aa4feb9564f9f98730b2a1
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08524900B2

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