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5-chloro-1-methyl-4-nitro-1H-pyrazole → HCID 58465025, Verbindung

HRID 2089357
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2089357
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][N:12]1[CH2:17][CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH2:14][CH2:13]1.C([O-])([O-])=O.[Na+].[Na+].CC([O-])=O.[K+]>CC#N.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]>[CH3:11][N:12]1[CH2:13][CH:14]=[C:15]([C:2]2[N:6]([CH3:7])[N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:16][CH2:17]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazoleHCID 207733711-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid, pinacol esterHCID 86658407Sodium carbonate potassium acetate

Produkt 1

HCID 58465025HCID 58465025, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
2×
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

5-Chloro-1-methyl-4-nitro-1H-pyrazole (0.2 g, 1.24 mmol), 1-methyl-1,2,3,6 tetrahydropyridine-4-boronic acid pinacol ester (0.553 g, 2.48 mmol) and Pd(dppf)2Cl2 (0.02 g, 0.025 mmol) were suspended in degassed MeCN (5 mL). Aqueous Na2CO3/KOAc solution (1:1, 1.1 M, 1.5 mL) was added and the mixture was heated at 130° C. in a microwave for 40 min. A further portion of Pd(dppf)2Cl2 (0.1 g, 0.12 mmol) was added and the mixture was heated at 130° C. for a further 90 min. The solvents were removed under reduced pressure and the crude residue dissolved in EtOAc and water. The mixture was extracted with EtOAc and the combined organic layers passed through a phase separator cartridge. The solvent was removed under reduced pressure and the crude product was purified via silica gel column chromatography (0-10% MeOH/DCM) to give 1-methyl-4-(1-methyl-4-nitro-1H-pyrazol-5-yl)-1,2,3,6-tetrahydropyridine as a brown oil (44 mg, 16%). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 5.89-5.86 (m, 1H), 3.82 (s, 3H), 3.19 (q, J=3.0 Hz, 2H), 2.74 (q, J=5.5 Hz, 2H), 2.47-2.39 (m, 5H)

Aufarbeitung

  1. temperaturethe mixture was heated at 130° C. for a further 90 min
  2. customThe solvents were removed under reduced pressure
  3. dissolutionthe crude residue dissolved in EtOAc
  4. extractionThe mixture was extracted with EtOAc
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified via silica gel column chromatography (0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-ddd6562a6ecd41d1a0d9b3231c015dd6
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08436001B2

Notizen zur Reaktion

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