Triphenylphosphine → 1-(2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)-3-phenylpropan-1-one

HRID 1408001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1408001
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1B1OC(C)(C)C(C)(C)O1)([O-:3])=[O:2].Br[C:26]1[CH:31]=[C:30]([C:32](=[O:41])[CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:29]=[CH:28][N:27]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C([O-])([O-])=O.[Na+].[Na+].C(COC)OC.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:6][C:5]=1[C:28]1[CH:29]=[C:30]([C:32](=[O:41])[CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:31]=[CH:26][N:27]=1)([O-:3])=[O:2]

Komponenten

8

Edukt 3

HCID 11776TriphenylphosphineHCID 66587487HCID 66587487, VerbindungHCID 867059361-(2-Bromopyridin-4-yl)-3-phenylpropan-1-one

Produkt 1

HCID 675181571-(2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)-3-phenylpropan-1-oneAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

A solution of 200 mg of 1-(4-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine 1.1e, 168 mg of 1-(2-bromopyridin-4-yl)-3-phenylpropan-1-one 5.1a, 12 mg of Pd(OAc)2, 58 mg of PPh3 in 1.25 mL of 2 N aqueous Na2CO3 solution and 3 mL of dimethoxyethane was refluxed for 4 h. The mixture was diluted with ethyl acetate and washed with water twice. The combined organic layer was dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed on silica gel eluting with a gradient of 0% to 7% ethyl acetate in dichloromethane to give 196 mg of product.

Aufarbeitung

  1. washwashed with water twice
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was chromatographed on silica gel eluting with a gradient of 0% to 7% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-bd6a3b6191084252bbde660ea77d52c7
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916569B2

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