Cesium carbonate → 2-Benzyloxy-6-sec-butylamino-isonicotinic acid methyl ester

HRID 732467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732467
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C@H:72]([NH2:76])([CH2:74][CH3:75])[CH3:73]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([NH:76][CH:72]([CH2:74][CH3:75])[CH3:73])[N:7]=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2724537(R)-sec-butylamineHCID 57930944Methyl 2-(benzyloxy)-6-chloroisonicotinate

Produkt 1

HCID 688149302-Benzyloxy-6-sec-butylamino-isonicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

Degas a sealed tube for 5 min and add a suspension 2-benzyloxy-6-chloro-isonicotinic acid methyl ester (1 g, 3.604 mmol), palladium acetate (100 mg, 0.445 mmol), racemic 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (307 mg, 0.493 mmol), cesium carbonate (1.2 g, 3.683 mmol) and (R)-sec-butylamine (0.5 mL, 1.387 mmol) in toluene (14 mL). Heat to 105° C. and stir for 20 h. Cool to room temperature, concentrate and purify (silica gel chromatography, eluting with 3:97 ethyl acetate:hexanes) to give the title compound.

Aufarbeitung

  1. customDegas a sealed tube for 5 min
  2. temperatureCool to room temperature
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 3:97 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-484d55b991c34dcdac414518d6e0c96b
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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