Potassium Phosphate, Tribasic → HCID 90333923, Verbindung

HRID 595708

Reaktionsgleichung

Reaktionsgleichung von HRID 595708
Br[C:2]1[C:3](=[O:9])[NH:4][NH:5][C:6](=[O:8])[CH:7]=1.[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14](B(O)O)[NH:15]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.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]>[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([C:2]1[C:3](=[O:9])[NH:4][NH:5][C:6](=[O:8])[CH:7]=1)[NH:15]2

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2549424-Bromopyridazine-3,6-diolHCID 90333436HCID 90333436, Verbindung

Produkt 1

HCID 90333923HCID 90333923, VerbindungAusbeute 40,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a degassed solution of 4-bromo-1,2-dihydropyridazine-3,6-dione (100 mg, 0.5 mmol), (4-fluoro-1H-indol-2-yl)boronic acid (131 mg, 0.7 mmol) and K3PO4 (279 mg, 1.1 mmol) in DMF (2 mL) and H2O (0.2 mL) was added Pd(dppf)Cl2 (5 mg) under N2. The mixture was stirred at 80° C. for 12 h. After the solvent was removed, the residue was purified by prep-TLC (DCM:EtOAc=10:1) to give the product of 4-(4-fluoro-1H-indol-2-yl)-1,2-dihydropyridazine-3,6-dione (50 mg, yield: 39%). 1H-NMR (DMSO-d6, 400 MHz) δ 11.95 (br. s, 1H), 7.47˜7.68 (m, 3H), 7.35 (d, J=8.0 Hz, 1H), 7.11˜7.19 (m, 1H), 6.81 (dd, J=8.0, 10.4 Hz, 1H). MS (M+H)+: 246.

Aufarbeitung

  1. customAfter the solvent was removed
  2. customthe residue was purified by prep-TLC (DCM:EtOAc=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-8e7c892558a24affa9fe7259afa67314
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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