Piperazine → HCID 56677001, Verbindung

HRID 68704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68704
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:17])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1>[CH3:17][C:6]1[C:5]2[C:9](=[CH:10][C:2]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:3][CH:4]=2)[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1

Komponenten

6

Edukt 4

HCID 4837PiperazineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 674498536-bromo-3-methyl-1-phenyl-1H-indazole

Produkt 1

HCID 56677001HCID 56677001, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-bromo-3-methyl-1-phenyl-1H-indazole (1 g, 3.50 mmol, 1.00 equiv) in toluene (20 mL), piperazine (600 mg, 6.98 mmol, 2.00 equiv), Cs2CO3 (1.7 g, 5.21 mmol, 1.50 equiv), Pd(AcO)2 (20 mg, 0.09 mmol, 0.03 equiv), BINAP (20 mg, 0.03 mmol, 0.03 equiv). The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting mixture was cooled, the solids were filtered out. The residue was applied onto a silica gel column with dichloromethane/methanol (20:1). The resulting residue (300 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed)): Column, SunFire Prep C18, 5 um, 19*100 mm; mobile phase, water with 0.05% TFA and MeOH (10% MeOH up to 42% in 4 min, hold 42% in 3.5 min, up to 100% in 0.1 min, hold 100% in 1.4 min); Detector, UV 220NMnm to yield 3-methyl-1-phenyl-6-(piperazin-1-yl)-1H-indazole as a light yellow solid.

Aufarbeitung

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting mixture was cooled
  4. filtrationthe solids were filtered out
  5. customThe resulting residue (300 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed))
  6. waitmobile phase, water with 0.05% TFA and MeOH (10% MeOH up to 42% in 4 min
  7. customin 3.5 min
  8. waitup to 100% in 0.1 min
  9. customin 1.4 min

Quellen und Nachweise

ORD-Eintrag
ord-56e06886d496447fb58077df8060d6db
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822447B2

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