HCID 178509964, Verbindung → 3,5-Dichloro-4-(7-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile

HRID 626707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626707
[N:1]([C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1/[CH:11]=[N:12]/[C:13]1[C:20]([Cl:21])=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=1[Cl:22])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:22][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([Cl:21])[C:13]=1[N:12]1[CH:11]=[C:5]2[CH:6]=[N:7][CH:8]=[C:9]([Cl:10])[C:4]2=[N:1]1)[C:17]#[N:18]

Komponenten

3

Edukt 1

HCID 178509964HCID 178509964, Verbindung

Produkt 1

HCID 696716223,5-Dichloro-4-(7-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 4-{[1-(4-azido-5-chloropyridin-3-yl)meth-(E)-ylidene]amino}-3,5-dichlorobenzonitrile (3.8 g, 10.95 mmol) in toluene (45 mL) was heated to reflux for 18 hours and then cooled to room temperature. The precipitated solid was removed by filtration and washed sequentially with toluene, ethyl acetate and DCM. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane) and then triturated with diethyl ether to afford the title compound as an off-white solid (2.5 g, 71% yield). 1H NMR (400 MHz, CDCl3): δ 9.30 (s, 1H), 8.46 (s, 1H), 8.42 (s, 1H), 7.86 (s, 2H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. customThe precipitated solid was removed by filtration
  4. washwashed sequentially with toluene, ethyl acetate and DCM
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane)
  7. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d2f2111e5527486bb52e47ae961f97e2
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309240B2

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