Water → 2-Fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-nicotinic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[N:6][C:5]=1[F:11].[F:13][C:14]([F:24])([F:23])[C:15]1[N:20]=[CH:19][C:18]([CH2:21][NH2:22])=[CH:17][CH:16]=1.O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:22][CH2:21][C:18]2[CH:19]=[N:20][C:15]([C:14]([F:24])([F:13])[F:23])=[CH:16][CH:17]=2)=[N:6][C:5]=1[F:11]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -40 °C
Versuchsvorschrift
To 2,6-difluoro-nicotinic acid methyl ester (60, 1.82 g, 0.0105 mol, prepared as described in Example 22, Scheme 24, Step 2) in N,N-dimethylformamide (20.0 mL), under an atmosphere of nitrogen at −40° C., C-(6-trifluoromethyl-pyridin-3-yl)-methylamine (561, 1.00 g, 5.68 mmol) was added. The reaction was stirred at −40° C., then allowed to warm to room temperature for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 35% to 100% ethyl acetate in hexane to give a white solid (562, 1.40 g, 74.9). MS (ESI) [M+H+]+=330.1.
Aufarbeitung
- temperatureto warm to room temperature for 2 hours
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated
- custompurified by silica gel column chromatography
- washeluting with 35% to 100% ethyl acetate in hexane
- customto give a white solid (562, 1.40 g, 74.9)
Quellen und Nachweise
- ORD-Eintrag
- ord-907008c58e164ba499b538e2cf56ff0b
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08722702B2
Notizen zur Reaktion
Wird geladen…