Potassium Carbonate → 3-[2-(1-t-Butyloxycarbonyl piperidin-4-yloxy)pyridin-5-yl]-1-(morpholin-4-yl)prop-2-ene-1-one

HRID 520815

Reaktionsgleichung

Reaktionsgleichung von HRID 520815
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[C:22]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)(=[O:25])[CH:23]=[CH2:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9]([O:8][C:5]2[CH:4]=[CH:3][C:2]([CH:24]=[CH:23][C:22]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])=[CH:7][N:6]=2)[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 98723AcryloylmorpholineHCID 21914479tert-Butyl 4-((5-bromopyridin-2-yl)oxy)piperidine-1-carboxylate

Produkt 1

HCID 900427223-[2-(1-t-Butyloxycarbonyl piperidin-4-yloxy)pyridin-5-yl]-1-(morpholin-4-yl)prop-2-ene-1-oneAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of t-butyl 4-(5-bromo pyridin-2-yloxy)piperidine-1-carboxylate (1 gram, 2.80 mmoles), 4-acryloylmorpholine (0.63 gram, 4.46 mmoles), palladium acetate (13 mg, 0.061 mmoles) tri(o-tolyl)phosphine (25.6 mg, 0.084 mmoles) and potassium carbonate (0.62 g, 4.49 mmoles) in DMF (15 mL) was stirred for 3 hours at 140° C. The progress of the reaction was monitored by thin layer chromtography. After completion of reaction, the mass was quenched on to chilled water (30 mL) and the product was extracted with ethyl acetate (3×15 mL). The resulting organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. The residue, thus obtained, was purified by flash chromatography using ethyl acetate:n-hexane in the ratio of 1:1 to afford the title compound (1.07 grams).

Aufarbeitung

  1. customAfter completion of reaction
  2. customthe mass was quenched on
  3. temperatureto chilled water (30 mL)
  4. extractionthe product was extracted with ethyl acetate (3×15 mL)
  5. washThe resulting organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue, thus obtained
  9. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-68b517314f804299a5a85ee2f2a0fa9c
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328092B2

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