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Water → tert-Butyl 4-(3-fluoro-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

HRID 1666472
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1666472
Br[CH:2]=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1COCC1.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]>[F:16][C:17]1[CH:18]=[C:19]([CH:20]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][N:25]=2)[CH:22]=1)[CH:2]=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 45489892tert-Butyl 4-(bromomethylidene)piperidine-1-carboxylateHCID 66876242HCID 66876242, Verbindung

Produkt 1

HCID 66877003tert-Butyl 4-(3-fluoro-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylateAusbeute 33,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of tert-butyl 4-(bromomethylene)piperidine-1-carboxylate (1.1 g, 0.0039 mol) in THF (13 mL) was added 3-fluoro-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenylboronic acid (1.4 g, 4.7 mmol), potassium phosphate (2.5 g, 0.012 mol) and H2O (0.23 mL) and the mixture was degassed using argon. PdCl2(dppf)2 (0.32 g, 0.4 mmol) was added and the mixture was degassed again. The reaction was heated at 50° C. for 1.5 h and then allowed to cool to RT. Water was added and the mixture was extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel column chromatography (2-4% ethyl acetate in hexane) to give the title compound (0.585 g, 19%). 1H NMR (500 MHz, CDCl3): δ 8.45 (s, 1H), 7.94 (d, J=8.6 Hz, 1H), 7.05 (d, J=8.65 Hz, 1H), 6.81-6.75 (m, 3H), 6.30 (s, 1H), 3.51 (t, J=5.55 Hz, 2H), 3.42 (t, J=5.6 Hz, 2H), 2.47 (t, J=5.55 Hz, 2H), 2.33 (m, 2H), 1.47 (s, 9H).

Aufarbeitung

  1. customthe mixture was degassed
  2. customthe mixture was degassed again
  3. temperatureto cool to RT
  4. additionWater was added
  5. extractionthe mixture was extracted with ethyl acetate three times
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness
  9. customThe residue was purified by silica gel column chromatography (2-4% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b76ad7754c9349dfbd72127dcbdbee9d
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08044052B2

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