Potassium Phosphate, Tribasic → HCID 58268026, Verbindung

HRID 244707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244707
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16](B4OC(C)(C)CC(C)(C)O4)[CH:15]=[C:14]([NH2:29])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:31]1[CH:32]=[C:33]2[CH:39]=[N:38][N:37]([S:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:34]2=[N:35][CH:36]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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.Cl[Pd]Cl.[Fe+2]>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16]([C:31]4[CH:32]=[C:33]5[CH:39]=[N:38][N:37]([S:40]([C:43]6[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=6)(=[O:41])=[O:42])[C:34]5=[N:35][CH:36]=4)[CH:15]=[C:14]([NH2:29])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 583564165-bromo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridineHCID 670292681-(Phenylsulfonyl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-1H-indazol-4-amine

Produkt 1

HCID 58268026HCID 58268026, VerbindungAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-(Phenylsulfonyl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-1H-indazol-4-amine (1.5 g, 3.63 mmol), 5-bromo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridine (1.350 g, 3.99 mmol), Pd(dppf)Cl2 (0.531 g, 0.726 mmol) and tripotassium phosphate (2.311 g, 10.89 mmol) were divided between 2 microwave vials and dissolved in 1,4-Dioxane (18 mL) and Water (6 mL); 9 ml dioxane and 3 ml water in each. Each vial was heated to 100° C. for 10 min in the microwave. Solvent was removed in vacuo and the residue was partitioned between DCM (100 ml) and water (100 ml). The organic layer was collected using a hydrophobic frit and the solvent was removed in vacuo. The residue was taken up in DCM (4 ml) and added to the top of 2×70 g silica SPE cartridges. These were subsequently eluted with 0-100% EtOAc/DCM over 40 mins. The product-containing fractions were combined to give the title compound as a pale yellow solid (581 mg).

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. customthe residue was partitioned between DCM (100 ml) and water (100 ml)
  3. customThe organic layer was collected
  4. customthe solvent was removed in vacuo
  5. additionadded to the top of 2×70 g silica SPE cartridges
  6. washThese were subsequently eluted with 0-100% EtOAc/DCM over 40 mins

Quellen und Nachweise

ORD-Eintrag
ord-8f347ca9bab246fdaa86f144aeff3e9a
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658635B2

Notizen zur Reaktion

Wird geladen…