Sodium Carbonate → 3-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine

HRID 238469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238469
CC1(C)COB([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)OC1.[CH3:20][N:21]1[CH2:26][CH:25]=[C:24](OS(C(F)(F)F)(=O)=O)[CH2:23][CH2:22]1.C([O-])([O-])=O.[Na+].[Na+]>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][N:21]1[CH2:22][CH:23]=[C:24]([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[CH2:25][CH2:26]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 113795771-Methyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonateHCID 219596073-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5-trifluoromethyl-phenylamine

Produkt 1

HCID 219596433-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5-trifluoromethyl-phenylamine (8.8 g, 0.032 mol) was added to trifluoro-methanesulfonic acid 1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl ester (7.91 g, 0.032 mol) and 2N Na2CO3 aqueous solution (25 mL) was bubbled through N2 for 5 min. Pd(PPh3)4 (3.7 g, 3.2 mmol) was added and the reaction was heated to 80° C. for 16 h. The reaction was cooled to RT and diluted with Et2O (100 mL). The mixture was filtered through Celite® and the filtrate was washed with NaHCO3 aqueous solution (25 ml) followed by brine (25 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. The desired product was isolated by passing through silica gel column chromatography (EtOAc, then (2M NH3) in MeOH/EtOAc) to provide a yellow oil.

Aufarbeitung

  1. customwas bubbled through N2 for 5 min
  2. temperatureThe reaction was cooled to RT
  3. filtrationThe mixture was filtered through Celite®
  4. washthe filtrate was washed with NaHCO3 aqueous solution (25 ml)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8e067ea7fe4646599350bd1bc37476b6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642624B2

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