Ethyl Acetate → 6-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine

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Reaktionsgleichung

[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]([CH3:20])[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:15]=2)=O)[C:5]([N+:21]([O-])=O)=[CH:4][N:3]=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[N:3]=[CH:4][C:5]2[NH:21][C:9]([C:11]3[N:12]([CH3:20])[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:15]=3)=[N:8][C:6]=2[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A solution of 5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid (2-bromo-5-nitro-pyridin-4-yl)-amide (79.8 mg, 0.183 mmol, prepared as described in the previous step) in acetic acid (1 mL) was treated with Fe powder (102 mg, 1.82 mmol). The resulting mixture was stirred at 110° C. for 1 h, cooled to room temperature, and treated with EtOAc (10 mL) and saturated NaHCO3 (10 mL). The organic layer was separated, washed with saturated NaHCO3 (10 mL), H2O (10 mL), concentrated, and the resulting residue dried in vacuo to yield 6-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine. 1H-NMR (400 MHz, CDCl3) δ: 10.0 (br s, 1H), 8.80 (br s, 1H), 7.60 (br s, 1H), 6.60 (m, 1H), 4.40 (s, 3H), 1.30 (s, 9H).

Aufarbeitung

temperaturecooled to room temperature
customThe organic layer was separated
washwashed with saturated NaHCO3 (10 mL), H2O (10 mL)
concentrationconcentrated
customthe resulting residue dried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-ab626a451f7a498f934a388a9c182619
Quelldatensatz: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09023846B2

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