Benzyl Alcohol → HCID 131735484, Verbindung

HRID 634431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634431
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5]([I:8])=[N:6][CH:7]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.CCCCCCC>[CH3:11][CH2:10][O:17][C:4]([CH3:5])=[O:9].[CH2:10]([O:9][C:4]1[C:5]([I:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 226029855-Bromo-2-iodopyridin-3-ol

Produkt 1

HCID 131735484HCID 131735484, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5-bromo-2-iodopyridin-3-ol (0.700 g, 2.334 mmol, prepared according to Bioorg. Med. Chem. Lett. 2013, 2, 6784, which is incorporated herein by reference in its entirety) in dry THF (10 ml), previously cooled to 0° C., benzyl alcohol (0.728 ml, 7.00 mmol), triphenylphosphine (PPh3) (2.095 ml, 7.00 mmol) and diisopropyl azodicarboxylate (1.287 ml, 6.54 mmol) were added. The reaction was stirred for 4 h at room temperature. Solvent was removed and the product was purified by Biotage Si 50 g with a gradient of heptane and EtOAc 3-(benzyloxy)-5-bromo-2-iodopyridine (Intermediate G25.1, 835 mg, 2.141 mmol, 92% yield) as a white foam.

Aufarbeitung

  1. customSolvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-b9eb90f9b7a346bf99552587be3751df
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321776B2

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