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Potassium Carbonate → 3-[5-(2-Methoxy-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid pyridazin-3-ylamine

HRID 1469379
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1469379
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19]([N:21]2[CH2:24][CH:23]([O:25][C:26]3[CH:31]=[CH:30][C:29](Br)=[CH:28][N:27]=3)[CH2:22]2)=[O:20])[N:13]=1.C(=O)([O-])[O-:34].[K+].[K+]>C1COCC1.O.C(OCC)(=O)C>[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[N:13]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:29]1[CH:30]=[CH:31][C:26]([O:25][CH:23]2[CH2:24][N:21]([C:19]([OH:20])=[O:34])[CH2:22]2)=[N:27][CH:28]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 667103553-(5-Bromo-pyridin-2-yloxy)-azetidine-1-carboxylic acid pyridazin-3-ylamide

Produkt 1

HCID 667104303-[5-(2-Methoxy-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid pyridazin-3-ylamineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857
Ethyl Acetate
Lösungsmittel
HCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2-methoxyphenyl boronic acid in THF/H2O (10:1; 40 mL) was added to a microwave vial containing 3-(5-bromo-pyridin-2-yloxy)-azetidine-1-carboxylic acid pyridazin-3-ylamide (prepared as in Example 19 Step 1) 1.5 g, 4.28 mmol) and potassium carbonate (1.78 g, 12.86 mmol). Nitrogen gas was bubbled through the mixture for 5 mins then 1,1′-bis[(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with CH2Cl2 (0.350 g, 10 mole %) was added and the vial sealed and heated at 100° C. in microwave synthesiser for 30 min. The cooled reaction mixture was diluted with ethyl acetate (100 mL) and washed sequentially with sat. aqueous sodium carbonate solution (100 mL) then sat. sodium chloride solution (100 mL). Mixture dried over magnesium sulphate and filtered. Filtrate solvents were removed in vacuo to afford a brown gum, which was purified by flash chromatography, eluting with a gradient of 80 to 100% ethyl acetate in hexane to a afford a pale yellow solid. Product was triturated with diethyl ether, filtered and dried to afford the title compound as a white solid (1.098 g, 68%)

Aufarbeitung

  1. customNitrogen gas was bubbled through the mixture for 5 mins
  2. addition1,1′-bis[(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with CH2Cl2 (0.350 g, 10 mole %) was added
  3. customthe vial sealed
  4. customThe cooled reaction mixture
  5. washwashed sequentially with sat. aqueous sodium carbonate solution (100 mL)
  6. dry with materialMixture dried over magnesium sulphate
  7. filtrationfiltered
  8. customFiltrate solvents were removed in vacuo
  9. customto afford a brown gum, which
  10. customwas purified by flash chromatography
  11. washeluting with a gradient of 80 to 100% ethyl acetate in hexane to
  12. customa afford a pale yellow solid
  13. customProduct was triturated with diethyl ether
  14. filtrationfiltered
  15. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ebb5cab6f13346baa9a249372aed988b
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09006269B2

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