Potassium Carbonate → N-{5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-fluorophenyl}-2,2,2-trifluoroacetamide

HRID 1159987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159987
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([F:23])=[C:14]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:15]=2)[CH:5]=[CH:4][N:3]=1.[I-].[NH2:25][N+:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:10]3[CH:11]=[CH:12][C:13]([F:23])=[C:14]([NH:16][C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])[CH:15]=3)=[N:25][N:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=23)[CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 59511388N-{5-[(2-Chloro-4-pyrimidinyl)ethynyl]-2-fluorophenyl}-2,2,2-trifluoroacetamide

Produkt 1

HCID 59511417N-{5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-fluorophenyl}-2,2,2-trifluoroacetamideAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-{5-[(2-chloro-4-pyrimidinyl)ethynyl]-2-fluorophenyl}-2,2,2-trifluoroacetamide (4.6 g, 13 mmol) in DMF (100 mL) was added aminopyridinium iodide (5.9 g, 27 mmol) and potassium carbonate (5.5 g, 40 mmol). After stirring 2 h at rt, the reaction mixture was diluted with diethyl ether (250 mL) and EtOAc (250 mL), and washed with water. The organic layer was adsorbed to silica gel and purified by column chromatography to afford the desired product (3.2 g, 55%) as a tan solid. 1H NMR (400 MHz, CDCl3): δ 8.57 (m, 2H), 8.31 (d, J=5.5 Hz, 1H), 8.14 (s, 1H), 7.47 (m, 2H), 7.31 (t, J=9.4 Hz, 1H), 7.04 (t, J=6.8 Hz), 6.99 (d, J=5.3 Hz, 1H). ES-LC/MS m/z=436 [M+H]+.

Aufarbeitung

  1. washwashed with water
  2. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-62b4a93fbb9b4503b75d060dc08795ea
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812022B2

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