Nitrogen → HCID 66929128, Verbindung

Temperatur

75 °C

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 1-[4-(4-nitro-pyrazol-1-ylmethyl)-pyridin-2-yl]-ethanone (250 mg, 1.01 mmol), iron powder (172 mg, 3.05 mmol) and NH4Cl (274 mg, 5.08 mmol) in a mixture of EtOH (4.0 mL) and water (2.0 mL) was stirred at 75° C. for 5 h. The reaction mixture was filtered while hot and the filter cake rinsed with EtOH. The filtrate was concentrated under reduced pressure and the residue partitioned between CH2Cl2 (10 mL) and aq. 1M NaOH (10 mL). The aq. layer was extracted with CH2Cl2 (2×10 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the title compound as a brown oil. TLC: rf (1:2 hept-EA)=0.05. LC-MS-conditions 02: tR=0.50 min, [M+H]+=217.47.

1. filtrationThe reaction mixture was filtered while hot and the filter cake
2. washrinsed with EtOH
3. concentrationThe filtrate was concentrated under reduced pressure
4. customthe residue partitioned between CH2Cl2 (10 mL) and aq. 1M NaOH (10 mL)
5. extractionThe aq. layer was extracted with CH2Cl2 (2×10 mL)
6. dry with materialextracts were dried over MgSO4
7. filtrationfiltered
8. customthe solvent removed under reduced pressure

ORD-Eintrag

ord-5eff5b1fa8b84695963c9acef1b8639c

Quelldatensatz

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08288419B2