3-Bromo-4-hydrazinylpyridine → 5-amino-1-(3-bromopyridin-4-yl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile

HRID 64326

Reaktionsgleichung

Reaktionsgleichung von HRID 64326
CO[C:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)=[C:4]([C:7]#[N:8])[C:5]#[N:6].[Br:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:28]=1[NH:29][NH2:30]>C(O)C>[NH2:6][C:5]1[N:29]([C:28]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[Br:22])[N:30]=[C:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)[C:4]=1[C:7]#[N:8]

Komponenten

4

Edukt 2

HCID 8171303-Bromo-4-hydrazinylpyridineHCID 223472272-((Methoxy)(4-phenoxyphenyl)methylene)malononitrile

Produkt 1

HCID 1176683205-amino-1-(3-bromopyridin-4-yl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrileAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(methoxy(4-phenoxyphenyl)methylene)malononitrile (7.3 g, 0.026 mol) and 3-bromo-4-hydrazinylpyridine (4.2 g, 0.022 mol) in ethanol (300 mL) was stirred at reflux under N2 overnight. The reaction was cooled to RT slowly and stirred at RT for about 4 hr till solid precipitated. The solid was filtered, collected and washed with hexane to get 3.38 g (35%) of 5-amino-1-(3-bromopyridin-4-yl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile as a light yellow solid. MS (ESI) m/e [M+1]+ 431.8, 433.8.

Aufarbeitung

  1. temperatureat reflux under N2 overnight
  2. stirringstirred at RT for about 4 hr till solid
  3. customprecipitated
  4. filtrationThe solid was filtered
  5. customcollected
  6. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-9f96f8727c5f4bf8ac4821bdaf5237f2
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447106B2

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