Dichloromethane → HCID 67410900, Verbindung

HRID 1481506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1481506
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[N:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1Br)=[O:5])[CH3:2].[C:17]([Cu])#[N:18].C(Cl)Cl>CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[N:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[C:17]#[N:18])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 147933444-bromo-5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl esterHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 67410900HCID 67410900, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 4-bromo-5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (1.00 g, 3.46 mmol) and CuCN (372 mg, 4.15 mmol) in NMP (10 mL) was stirred at 200° C. under microwave irradiation for 1 h. After cooling to room temperature, the mixture was treated with DCM (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (0:100-10:90 EtOAc-hexanes) to yield the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 4.45 (q, J=7.2 Hz, 2H), 4.14 (s, 3H), 1.45 (t, J=7.2 Hz, 3H), 1.43 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C12H17N3O2: 236.1 (M+H). Measured: 236.1.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography on silica gel (0:100-10:90 EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-523f5aa14cb24dc7bf31f978ee867ad3
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409915B2

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