Hydrazine hydrate (1:1) → 5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-amine

HRID 571898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571898
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9](F)=[C:10]([CH:13]=1)[C:11]#[N:12].O.[NH2:20][NH2:21]>C(O)CCC.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH2:5][C:6]1[CH:13]=[C:10]2[C:9](=[CH:8][CH:7]=1)[NH:21][N:20]=[C:11]2[NH2:12]

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 441342595-(3,5-Difluorobenzyl)-2-fluorobenzonitrile

Produkt 1

HCID 441342655-[(3,5-difluorophenyl)methyl]-1H-indazol-3-amineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-(3,5-difluoro-benzyl)-2-fluoro-benzonitrile (20 g, 80.9 mmol) and hydrazine hydrate (19.6 mL, 404 mmol) in n-butanol (200 mL) was heated at 120° C. overnight. The reaction mixture was diluted with water/ethyl acetate and the organic phase washed twice with brine, dried and evaporated. Crude was triturated with diethyl ether and filtered to afford 13 gr of final product. Purification of the resulting organic phase by chromatography over silica gel (DCM/EtOH 95:5) afforded further 6.3 g of the title compound (total amount 19.2 g, 92% yield).

Aufarbeitung

  1. washthe organic phase washed twice with brine
  2. customdried
  3. customevaporated
  4. customCrude was triturated with diethyl ether
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-653c26853bc740debaa494ab5ed294b7
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029356B2

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