Potassium Carbonate → HCID 68936624, Verbindung

HRID 1260946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260946
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([N:18]([CH3:29])[C:19](=[O:28])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C@H:14]([C:30]3[CH:35]=[CH:34][C:33](Br)=[CH:32][CH:31]=3)[CH2:13]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:37]1(B(O)O)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([N:18]([CH3:29])[C:19](=[O:28])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C@H:14]([C:30]3[CH:35]=[CH:34][C:33]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:32][CH:31]=3)[CH2:13]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

9

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 68935939HCID 68935939, Verbindung

Produkt 1

HCID 68936624HCID 68936624, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of the compound obtained in Example 239 (0.20 g), phenylboronic acid (0.066 g), dppf (0.040 g), Pd(OAc)2 (0.008 g) and potassium carbonate (0.050 g) in toluene (3 mL), water (0.3 mL) and DMF (1 mL) was stirred under an argon atmosphere at 100° C. for 10 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine, and concentrated. The residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 65→95% ethyl acetate/hexane) to give the title compound (0.12 g, 61%) as a white powder.

Aufarbeitung

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 65→95% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-12a8e50719744708889c2dc733f2bcb2
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470816B2

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