2,9-Dimethyl-1,10-phenanthroline → 4-(6-Amino-pyridin-3-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2264351

Reaktionsgleichung

Reaktionsgleichung von HRID 2264351
CC1C=CC2C(=C3C(=CC=2)C=CC(C)=N3)N=1.CC(C)([O-])C.[Na+].[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([SH:36])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].[Mg].[NH2:38][C:39]1[CH:44]=[CH:43][C:42](I)=[CH:41][N:40]=1>[Cu]I.C1(C)C=CC=CC=1>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([S:36][C:42]2[CH:41]=[N:40][C:39]([NH2:38])=[CH:44][CH:43]=2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Komponenten

8

Edukt 5

HCID 652372,9-Dimethyl-1,10-phenanthrolineHCID 885792-Pyridinamine, 5-iodo-HCID 5462224MagnesiumHCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylateHCID 23676156Sodium t-butoxide

Produkt 1

HCID 674273204-(6-Amino-pyridin-3-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl esterAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Add dry toluene (6.06 mL) to a mixture of 2,9-dimethyl-1,10-phenanthroline (76.52 mg), copper(I) iodide (69.27 mg), sodium tert-butoxide (475.59 mg), 4-mercapto-piperidine-1-carboxylic acid tert-butyl ester (583.5 mg), magnesium (49.10 mg) and 2-amino-5-iodopyridine (550 mg). Bubble nitrogen into the mixture with ultrasound and stir the suspension at 110° C. in a sealed tube for 24 h. Cool and filter through celite. Wash with toluene and remove the solvent under vacuum. Add hexane/EA (1/1) and filter through a celite/silica gel pad, washing twice with hexane/EA (1/1) and then EA. Remove the solvent under vacuum. Purify by silica gel column chromatography eluting with hexane/EA (50-75%) to afford 630 mg of the title compound. MS (ES+): m/z=310 (M+H)+

Aufarbeitung

  1. temperatureCool
  2. filtrationfilter through celite
  3. washWash with toluene
  4. customremove the solvent under vacuum
  5. filtrationAdd hexane/EA (1/1) and filter through a celite/silica gel pad
  6. washwashing twice with hexane/EA (1/1)
  7. customRemove the solvent under vacuum
  8. customPurify by silica gel column chromatography
  9. washeluting with hexane/EA (50-75%)

Quellen und Nachweise

ORD-Eintrag
ord-bee74f59518041d09dfddf5b94f00686
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855211B2

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