Boron tribromide → (E)-methyl 3-(5-((6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate

HRID 632691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632691
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[N:16][CH:17]=3)=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=3)[S:8][C:7]=2[CH:32]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[N:16][CH:17]=3)=[C:9]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[S:8][C:7]=2[CH:32]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 86730673HCID 86730673, Verbindung

Produkt 1

HCID 136341396(E)-methyl 3-(5-((6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (E)-methyl 3-(5-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate (0.096 g, 0.215 mmol) in DCM (2.145 mL) at room temperature was added BBr3 (1.0 M in heptane, 0.858 mL, 0.86 mmol) and the reaction was stirred at room temperature for 30 min. Upon completion the reaction was quenched with MeOH (2.0 mL) and stirred for 10 min at room temperature then concentrated in vacuo onto silica gel then purified by column chromatography (SiO2, 0-20% MeOH/DCM) to afford (E)-methyl 3-(5-((6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate. LC/MS (m/z, MH+): 420.3.

Aufarbeitung

  1. customUpon completion the reaction was quenched with MeOH (2.0 mL)
  2. stirringstirred for 10 min at room temperature
  3. concentrationthen concentrated in vacuo onto silica gel
  4. customthen purified by column chromatography (SiO2, 0-20% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-4124f9f2011446c18951fb5292ff462c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321746B2

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