Sodium Carbonate → HCID 67185001, Verbindung

HRID 1020021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020021
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1B(O)O.[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH:25]([C:29](=[O:38])[NH:30][C:31]2[CH:36]=[C:35](Cl)[N:34]=[CH:33][N:32]=2)[CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH:25]([C:29](=[O:38])[NH:30][C:31]2[CH:36]=[C:35]([C:3]3[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[N:34]=[CH:33][N:32]=2)[CH2:24]1)=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 3294524(2-Fluoro-6-methoxyphenyl)boronic acidHCID 86645892HCID 86645892, Verbindung

Produkt 1

HCID 67185001HCID 67185001, VerbindungAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-fluoro-6-methoxyphenyl boronic acid (0.20 g, 1.1 mmol) in a mixture of THF and water (6 ml, 1:1), 3-(6-chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (0.35 g, 0.93 mmol) was added at 0° C. followed by palladium acetate (12 mg, 54 μmol), PPh3 (31 mg, 0.12 mmol) and saturated solution of sodium carbonate (2 ml). The reaction mixture was stirred at room temperature for 30 h and then filtered through a celite bed which was washed with ethyl acetate. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with brine, dried and evaporated under reduced pressure. The crude product was purified by column chromatography, using hexane/ethyl acetate (4:1) as eluent, to provide 0.31 g (yield: 66.7%) of 3-[6-(2-fluoro-6-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester.

Aufarbeitung

  1. additionwas added at 0° C.
  2. filtrationfiltered through a celite bed which
  3. washwas washed with ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-551eb81421fa4d78bd1175747fb94d37
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716296B2

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