2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → 4-{[tert-butyl(dimethyl)silyl]oxy}-1-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidine

HRID 1808743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808743
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Si:13]([O:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[Si:13]([O:20][CH:21]1[CH2:22][CH2:23][N:24]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N:8]3[CH:12]=[CH:11][N:10]=[N:9]3)[CH:3]=2)[CH2:25][CH2:26]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Komponenten

7

Edukt 4

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 114813284-((Tert-butyldimethylsilyl)oxy)piperidineHCID 131061071-(3-Bromophenyl)-1H-1,2,3-triazoleHCID 23676156Sodium t-butoxide

Produkt 1

HCID 706645084-{[tert-butyl(dimethyl)silyl]oxy}-1-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A dioxane (5 mL) solution of 1-(3-bromophenyl)-1H-1,2,3-triazole (224 mg, 1.00 mmol) and 4-{[tert-butyl(dimethyl)silyl]oxy}piperidine (323 mg, 1.50 mmol) was degassed with bubbling nitrogen in a vial. 2-(Dicyclohexylphosphino)-2′-(dimethylamino)biphenyl (20 mg, 0.051 mmol), palladium(II)acetate (11 mg, 0.050 mmol), and sodium tert-butoxide (384 mg, 4.0 mmol) were then added. The reaction mixture was degassed again, and the vial was sealed. It was heated to 100° C. for 20 hours and allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound. 1H NMR (500 MHz, CDCl3) δ 7.96 (s, 1H), 7.83 (s, 1H), 7.38-7.31 (m, 2H), 7.02 (d, J=7.9 Hz, 1H), 6.98 (d, J=8.5 Hz, 1H), 3.97-3.89 (m, 1H), 3.53 (ddd, J=12.4, 7.5, 3.5 Hz, 2H), 3.16 (ddd, J=12.5, 7.8, 3.5 Hz, 2H), 1.95-1.81 (m, 2H), 1.72-1.64 (m, 2H), 0.90 (s, 9H), 0.08 (s, 6H); LC-MS: m/z 359.1 (M+H).

Aufarbeitung

  1. customThe reaction mixture was degassed again
  2. customthe vial was sealed
  3. temperatureto cool to room temperature
  4. additionThe reaction mixture was diluted with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washChromatography over silica gel, eluting with hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6b318f2c63bd4c38bbf797832ad1f27c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08361994B2

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