Triazole substituted aminobenzophenone compounds
A compound, ketone technology, applied in the field of triazole-substituted aminobenzophenone
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preparation example 1
[0285] 2-Methyl-5-nitro-thiobenzoic acid S-pyridin-2-yl ester (compound 401)
[0286] Dissolve 2-methyl-5-nitrobenzoic acid (22.5 g, 124 mmol), 2,2'-dithiopyridine (27.5 g, 124 mmol) and triphenylphosphine (32.6 g, 124 mmol) in 3 CN (650 mL). The solution was stirred at room temperature for 18 h. The reaction mixture was filtered and the solid was washed with a small amount of CH 3 CN washes. The title compound was obtained as a colorless solid.
preparation example 2
[0288] (4-bromo-2-chloro-phenyl)-(2-methyl-5-nitro-phenyl)-methanone (compound 402)
[0289] The reaction was performed in dry glassware under an argon atmosphere.
[0290] 4-Bromo-2-chloroiodobenzene (25.5 g, 80.9 mmol) was dissolved in anhydrous THF (400 mL) and cooled to -60 °C. Under stirring, isopropylmagnesium chloride (2M solution in THF, 40.4 mL, 80.9 mmol) was added thereto within 30 minutes. The reaction mixture was warmed to -40°C and the mixture was stirred at -40°C for 4h. Compound 401 (22.2 g, 80.9 mmol) was added thereto and the mixture was stirred at -40°C for 3 h, after which it was warmed to room temperature and stirred for 17 h. Add NH to it 4 Saturated aqueous Cl solution (200 mL) and the mixture was stirred for 1 h. The phases were separated and the aqueous phase was washed with Et 2 O (4x100 mL) for extraction. The combined organic phases were washed with brine, dried (MgSO 4 ), filtered and concentrated in vacuo. The crude product was purified ...
preparation example 3
[0292] [2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone (compound 403)
[0293] Compound 402 (5.4 g, 15.2 mmol) was dissolved in anhydrous 1,4-dioxane (150 mL) in a 200 mL screw cap container. To this was added 2,4-difluoroaniline (1.7 mL, 16.7 mmol) and argon was blown over the mixture. Add Cs to it 2 CO 3 (14.9g, 45.7mmol), BINAP (0.38g, 0.6mmol) and Pd(OAc) 2 (0.14 g, 0.6 mmol) and argon was blown through the mixture, and the vessel was closed. The mixture was stirred at 100 °C for 7 h. The reaction mixture was poured into H 2 O (100 mL) and EtOAc (200 mL). The aqueous phase was extracted with EtOAc (x3) and the combined organic phases were washed with brine, dried (MgSO 4 ), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography with CH 2 Cl 2 / petroleum ether (40-60) 2:3->1:1->1:0, then EtOAc as eluent gave the title compound as a yellow crystalline compound.
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