4-Nitrobenzoyl chloride → N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-nitrobenzamide

HRID 2390820Notizen

Reaktionsgleichung

[C:1]([C:5]1[C:6]([O:20][CH3:21])=[C:7]([NH2:19])[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>C(Cl)Cl>[C:1]([C:5]1[C:6]([O:20][CH3:21])=[C:7]([NH:19][C:29](=[O:30])[C:28]2[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:33][CH:32]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

step 3—To a solution of 100 (0.24 g, 0.85 mmol) and TEA (0.18mL, 1.3 mmol) in DCM (10 mL) at 0° C. was added 4-nitrobenzoyl chloride (0.19 g, 1.0 mmol). The resulting mixture was stirred at 0° C. for 3 h, and then warmed to RT. The mixture was then diluted with additional DCM, washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated. The crude residue so obtained was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.36 g (97%) of N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-nitrobenzamide (102) as a light yellow solid.

Aufarbeitung

temperaturewarmed to RT
washwashed sequentially with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe crude residue so obtained
customwas purified by SiO2 chromatography
washeluting with EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag: ord-f7ce140d8c5541ecb67439d7a3f681d7
Quelldatensatz: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08273773B2

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