Cesium carbonate → tert-Butyl 4-(3-(5-(2,2,2-trifluoroethoxy)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

HRID 1666414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666414
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1.[F:29][C:30](I)([F:32])[F:31].[C:34]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[F:29][C:30]([F:32])([F:31])[CH2:34][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 16843TrifluoroiodomethaneHCID 66875736tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Produkt 1

HCID 66875845tert-Butyl 4-(3-(5-(2,2,2-trifluoroethoxy)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylateAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of tert-butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.8 g, 2.09 mmol) in DMF (5 mL) cooled to 0° C. was added trifluoromethyliodide (548.9 mg, 2.614 mmol) and Cs2CO3 (1.3 gm, 4.18 mmol). The reaction mixture was stirred at 80° C. overnight. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate three times. The organic layer was washed with water and brine solution, dried over Na2SO4 and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (1:19 acetone:hexane) to give the title compound (360 mg, 37%). 1H NMR (500 MHz, CDCl3): δ 7.91 (d, J=2.8 Hz, 1H), 7.31 (m, 2H), 7.0 (d, J=7.75 Hz, 1H), 6.89 (m, 3H), 6.33 (s, 1H), 4.33 (q, J=8 Hz, 2H), 3.49 (m, 2H), 3.39 (m, 2H), 2.45 (m, 2H), 2.31 (m, 2H), 1.47 (s, 9H); m/z (465.1, M+ H+).

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with water and brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (1:19 acetone:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d6c9ecc9debf4ff29b7bcf3d496fda45
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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