2,5-Dibromopyridine → HCID 59643333, Verbindung

HRID 2251524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251524
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][N:32]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[Br:37][C:34]1[CH:35]=[CH:36][C:31]([N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=2)[CH2:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:12]=2)=[N:32][CH:33]=1

Komponenten

5

Edukt 3

HCID 693532,5-DibromopyridineHCID 81531Diisopropylethylamine2×HCID 59643115HCID 59643115, Verbindung

Produkt 1

HCID 59643333HCID 59643333, VerbindungAusbeute 18,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (3 g; 7.3 mmol) in 7 ml of dioxane was treated under nitrogen with 2,5-dibromopyridine (1.9 g; 8.1 mmol) and DIEA (1.4 ml; 8.1 mmol) and heated in a pressure tube for 2 days at 210C. Upon cooling, additional DIEA (1.4 ml) was added and heated 2 more days. Upon cooling, the reaction mixture was partitioned between ethyl acetate and 0.5N HCl. The organic phase was washed with 0.5N HCl and saturated brine, dried over sodium sulfate and concentrated. Purification by silica gel chromatography using an ethyl acetate-hexane gradient (5–60%) afforded the title compound (0.75 g; 18% yield).

Aufarbeitung

  1. temperatureUpon cooling
  2. temperatureheated 2 more days
  3. temperatureUpon cooling
  4. customthe reaction mixture was partitioned between ethyl acetate and 0.5N HCl
  5. washThe organic phase was washed with 0.5N HCl and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a7b334ceef544331852cb738416c0d21
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319104B2

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