Triphenylphosphine → 2-(4-(5-phenyl-2H-tetrazol-2-yl)but-1-ynyl)pyridine

HRID 1189074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189074
[C:1]1([C:7]2[N:8]=[N:9][NH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[C:19][CH2:20][CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[N:9][N:10]([CH2:21][CH2:20][C:19]#[C:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 874255-Phenyl-1H-tetrazoleHCID 110080634-(Pyridin-2-yl)but-3-yn-1-ol

Produkt 1

HCID 116447802-(4-(5-phenyl-2H-tetrazol-2-yl)but-1-ynyl)pyridineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 5-phenyl-2H-tetrazole (330 mg, 2.2 mmol), 4-(pyridin-2-yl)but-3-yn-1-ol (220 mg, 1.49 mmol) and triphenylphosphine polymer supported (750 mg, 2.2 mmol, loading 3mmol/g) were dissolved DCM (3 mL) and stirred at 0° C. Diisoprpylazodicarboxylate (452 mg, 2.2 mmol) was added dropwise, at 0° C. over a period of 30 min. The reaction mixture was then warmed to room temperature and stirred over night. The reaction mixture was filtered through celite and the cake was washed with DCM. The combined organic layers were washed with aqueous ammoniac, brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (prepacked 25g silicagel column, DCM 100% as eluent) to afford 209 mg of 2-(4-(5-phenyl-2H-tetrazol-2-yl)but-1-ynyl)pyridine (Yield: 51%) as a pink powder (M.P.=71-73° C.).

Aufarbeitung

  1. additionwas added dropwise, at 0° C. over a period of 30 min
  2. temperatureThe reaction mixture was then warmed to room temperature
  3. stirringstirred over night
  4. filtrationThe reaction mixture was filtered through celite
  5. washthe cake was washed with DCM
  6. washThe combined organic layers were washed with aqueous ammoniac, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography (prepacked 25g silicagel column, DCM 100% as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-6cc049524b27450a860bb43d84024a70
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674106B2

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