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Potassium bis(trimethylsilyl)amide → 4-((6-Bromo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)oxy)benzonitrile

HRID 520835
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 520835
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:24])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(=O)=O.CC(C)=O>C1COCC1>[Br:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][C:13](=[O:24])[C:14]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1)=[C:7]2[OH:8]
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Komponenten

5

Edukt 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 8112554Methyl 5-bromo-2-(2-(4-cyanophenoxy)acetamido)benzoate2×HCID 18522661Acetone cardice

Produkt 1

HCID 867154554-((6-Bromo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)oxy)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a suspension of methyl 5-bromo-2-(2-(4-cyanophenoxy)acetamido)benzoate (0.240 g, 0.617 mmol, Intermediate 2: step b) in THF (6.65 mL) at −78° C. was added potassium bis(trimethylsilyl)amide (0.5 M in toluene, 3.66 mL, 1.83 mmol) over 1.5 minutes, and the mixture was stirred for 5 minutes. The dry-ice/acetone bath was replaced with wet-ice bath and the reaction was stirred for 1.5 hours. The reaction was then quenched with water and ethyl acetate was added. The organic layer was removed and the aqueous layer was acidified with 2 N HCl (kept pH above 2). An off-white precipitate was formed which was filtered and the solid was dried overnight in the air and 1 hour in an oven at 40° C. to give the title compound.

Aufarbeitung

  1. stirringthe reaction was stirred for 1.5 hours
  2. customThe reaction was then quenched with water and ethyl acetate
  3. additionwas added
  4. customThe organic layer was removed
  5. customAn off-white precipitate was formed which
  6. filtrationwas filtered
  7. customthe solid was dried overnight in the air and 1 hour in an oven at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-958ee5eeb18142cb8afc3859721c2774
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09328095B2

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