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Sodium Bicarbonate → (4-Cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-[4-(2,5-dichloro-4-hydroxymethyl-phenoxy)-pyridin-3-yl]-methanone

HRID 1025880
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1025880
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18]([N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH:30]3[CH2:32][CH2:31]3)[CH2:22][CH2:21]2)=[O:19])=[CH:6][C:5]=1[Cl:33].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:30]1([N:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:20]([C:18]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3[O:11][C:7]3[CH:6]=[C:5]([Cl:33])[C:4]([CH2:3][OH:2])=[CH:9][C:8]=3[Cl:10])=[O:19])[CH2:21][CH2:22]2)[CH2:31][CH2:32]1
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Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 533121122,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester

Produkt 1

HCID 53311273(4-Cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-[4-(2,5-dichloro-4-hydroxymethyl-phenoxy)-pyridin-3-yl]-methanoneAusbeute 26,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.10 g (0.20 mmol) 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester (Example 27) in 1 mL tetrahydrofuran was added 0.008 g (0.21 mmol) lithium aluminium hydride. The resulting suspension was stirred at room temperature for 2.5 hours, poured on aqueous saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated to dryness. The resulting powder was purified by silica gel chromatography using a MPLC system (10 g silica gel column, CombiFlash Companion, Isco Inc.) with a gradient of n-heptane:ethyl acetate (100:0 to 50:50) to give 0.025 g (26%) of the desired compound as a light brown oil. MS (ESI): m/z=470.103 [M+H]+.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated to dryness
  7. customThe resulting powder was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8cae39653460401f9e4b4b87ce9b9f18
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729091B2

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