1-(2-methoxy-2-methyl-propyl)-3-nitro-1H-pyrazole → HCID 66899934, Verbindung

HRID 546179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546179
[CH3:1][O:2][C:3]([CH3:14])([CH3:13])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[N:6]1.[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]([CH3:14])([CH3:13])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([NH2:10])=[N:6]1

Komponenten

5

Edukt 2

HCID 668993201-(2-methoxy-2-methyl-propyl)-3-nitro-1H-pyrazoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 66899934HCID 66899934, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

In a Parr shaker bottle was placed 1-(2-methoxy-2-methyl-propyl)-3-nitro-1H-pyrazole (1.33 g, 6.68 mmol), 10% palladium on activated carbon (135 mg) and ethanol (50 mL). The bottle was then placed on the Parr shaker at 50 psi of hydrogen pressure for 2 h. The reaction was then filtered through a pad of celite and washed with ethanol and concentration in vacuo with silica gel (3 g) and purified on Biotage Flash chromatography system (40S column, silica gel, 5% methanol/ethyl acetate) to afford 1-(2-methoxy-2-methyl-propyl)-1H-pyrazol-3-ylamine (802 mg, 71%) as a colorless oil: ES-HRMS m/e calcd for C23H33N3O5S (M+H)+ 464.2214, observed 464.2208; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04 (s, 6H, 2×CH3), 3.13 (s, 3H, OCH3), 3.80 (s, 2H, NCH2), 4.48 (brs, 2H, NH2), 5.38 (d, J=2.3 Hz, 1H, Ar), 7.21 (d, J=2.3 Hz, 1H, Ar).

Aufarbeitung

  1. filtrationThe reaction was then filtered through a pad of celite
  2. washwashed with ethanol and concentration in vacuo with silica gel (3 g)
  3. custompurified on Biotage Flash chromatography system (40S column, silica gel, 5% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ceac89d7b39a43f7a3b4e61c5815b1ce
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935699B2

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