1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 66799298, Verbindung

HRID 1193382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193382
[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:19][O:20][C:21]1[CH:26]=[C:25](Br)[CH:24]=[CH:23][N:22]=1.C(O[Na])CCC.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([N:16]2[CH2:15][CH2:14][CH:13]([N:2]([CH3:1])[C:3](=[O:12])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:18][CH2:17]2)[CH:24]=[CH:23][N:22]=1

Komponenten

7

Edukt 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 140623094-Bromo-2-methoxypyridineHCID 18677746Benzyl methyl(piperidin-4-yl)carbamateHCID 178454433HCID 178454433, Verbindung

Produkt 1

HCID 66799298HCID 66799298, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (1.43 mmol, 1.0 eq.), 2-methoxy-4-bromopyridine and BuONa (411 mg, 4.29 mmol, 3.0 eq.) were taken up in toluene (20 ml) and degassed with argon. Xantphos (50 mg, 0.085 mmol, 0.06 eq.) and Pd2(dba)3 (26 mg, 0.028 mmol, 0.02 eq.) were then added and the mixture was heated for 16 hours at 90° C. After monitoring by TLC, the reaction mixture was concentrated and the residue was taken up in DCM (100 ml), washed with water and sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 0.5% MeOH in DCM). Yield: 51% (260 mg, 0.732 mmol)

Aufarbeitung

  1. customdegassed with argon
  2. concentrationthe reaction mixture was concentrated
  3. washwashed with water and sat. NaCl solution (50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, 0.5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-079376f175654289856fec06e7fff119
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

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