Tetrahydrofuran → 2-Methyl-6-[(1-methylpiperidin-4-yl)-methyl]-3-nitropyridine

HRID 1672211

Reaktionsgleichung

Reaktionsgleichung von HRID 1672211
B1C2CCCC1CCC2.C1COCC1.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=[CH2:22])[CH2:18][CH2:17]1.C[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[C:26]([CH3:33])[N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:33][C:26]1[C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=[C:24]([CH2:22][CH:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[N:25]=1

Komponenten

8

Edukt 5

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 849582,6-Dimethyl-3-nitropyridineHCID 139537Piperidine, 1-methyl,4-methylene-

Produkt 1

HCID 584766172-Methyl-6-[(1-methylpiperidin-4-yl)-methyl]-3-nitropyridineAusbeute 11,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 9-BBN in THF (0.5 M, 4.93 mL, 2.46 mmol) was added 1-methyl-4-methylenepiperidine (274 mg, 2.46 mmol). The reaction mixture was allowed to stir at 75° C. for 1 h and was then allowed to cool to rt. The resulting solution was transferred into a solution of 2-methyl-5-nitro-6-methylpyridine (486 mg, 2.24 mmol) in DMF (11 mL). To the mixture were added [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1:1 complex with DCM, 54.9 mg, 0.0672 mmol) and potassium carbonate (402 mg, 2.91 mmol). The reaction mixture was allowed to stir for 3 h at rt. The mixture was quenched by the addition of water (10 mL). The aqueous solution was extracted with DCM. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 2-methyl-6-[(1-methylpiperidin-4-yl)-methyl]-3-nitropyridine (64 mg, 10%) as a white solid. LCMS (FAL): Rt=3.38 min, m/z=250.2 (M+H).

Aufarbeitung

  1. temperatureto cool to rt
  2. stirringto stir for 3 h at rt
  3. customThe mixture was quenched by the addition of water (10 mL)
  4. extractionThe aqueous solution was extracted with DCM
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7263473b6ffe4bc2960ab44f38b0b37d
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998952B2

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