Potassium Phosphate, Tribasic → HCID 45269229, Verbindung

HRID 659710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659710
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:9]1([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([OH:21])[CH:15]=2)[CH2:11][CH2:10]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C(CCC)=CC(CCC)=CC=1CCC)(C)(C)C.Cl[C:54]1[C:55]2[CH:64]=[N:63][N:62]([C:65]3[CH:70]=[CH:69][CH:68]=[C:67]([F:71])[CH:66]=3)[C:56]=2[N:57]([CH3:61])[C:58](=[O:60])[CH:59]=1>C1COCC1.C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:9]1([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([O:21][C:54]3[C:55]4[CH:64]=[N:63][N:62]([C:65]5[CH:70]=[CH:69][CH:68]=[C:67]([F:71])[CH:66]=5)[C:56]=4[N:57]([CH3:61])[C:58](=[O:60])[CH:59]=3)[CH:15]=2)[CH2:10][CH2:11]1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 28390692HCID 28390692, VerbindungHCID 57708073HCID 57708073, VerbindungHCID 67346612HCID 67346612, Verbindung

Produkt 1

HCID 45269229HCID 45269229, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In sealed a glass tube, a mixture of potassium phosphate tribasic (251 mg, 1.18 mmol), tris(dibenzylideneacetone)dipalladium (0) (14 mg, 0.015 mmol), N-cyclopropyl-3-hydroxy-4-methylbenzamide (136 mg, 0.71 mmol), 2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (14 mg, 0.032 mmol) and 4-chloro-1-(3-fluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (164 mg, 0.59 mmol) in THF (0.5 mL) and toluene (1.30 mL) was heated at 110° C. in an oil bath for 18 h. The reaction mixture was cooled to RT, quenched with saturated ammonium chloride, and extracted twice with EtOAc. The combined EtOAc layers were washed with brine, dried and concentrated. The resulting crude material was purified on an ISCO (12 g column) eluting with a solvent gradient of 50-90% EtOAc in hexanes, to afford the title compound as a tan amorphous solid. MS (ESI, pos.ion) m/z: 433.0 (M+1).

Aufarbeitung

  1. customIn sealed a glass tube
  2. temperatureThe reaction mixture was cooled to RT
  3. customquenched with saturated ammonium chloride
  4. extractionextracted twice with EtOAc
  5. washThe combined EtOAc layers were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting crude material was purified on an ISCO (12 g column)
  9. washeluting with a solvent gradient of 50-90% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f719707ac19445f49e9ae54825c4dd71
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080546B2

Notizen zur Reaktion

Wird geladen…