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In dimethyl sulfoxide; at 20.0℃; for 3.0h;Inert atmosphere;
NaOMe (9.5 g) was added portion wise to a solution of 2-bromo-3,4-difluoro-1 -nitrobenzene (21.0 g) dissolved in DMSO (250 ml) at room temperature under nitrogen atmosphere. The mixture was stirred for 3 hrs and then poured onto water and extracted with ethyl acetate. The organic phase was extracted with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product, 2-bromo-3-fluoro-4-methoxy-1-nitro-benzene was used as such in Step 2 described below. 1H NMR (CDCI3) delta ppm: 7.85 (1H, dd); 6.99 (1 H, dd); 3.99 (3H, s).
2-bromo-3-fluoro-1-nitro-4-phenoxybenzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
With potassium carbonate; N,N-dimethyl-formamide; at 80.0℃;
To a mixture of a 2-bromo-3,4-difluoro- 1 -nitrobenzene (15.8 g, 66.4 mmol) and potassium carbonate (18.3 g, 132.8 mmol) in DMF (50 mL) was added phenol (6.25 g, 66.4 mmol) followed by stirring at 80 C overnight. The title compound was collected by adding water to the reaction mixture and filtering to isolate a yellow solid (18 g, 87%).
87%
With potassium carbonate; In N,N-dimethyl-formamide; at 80.0℃;
To a mixture of a <strong>[350699-92-2]2-bromo-3,4-difluoro-1-nitrobenzene</strong> (15.8 g, 66.4 mmol) and potassium carbonate (18.3 g, 132.8 mmol) in DMF (50 mL) was added phenol (6.25 g, 66.4 mmol) followed by stirring at 80 overnight. The title compound was collected by adding water to the reaction mixture and filtering to isolate a yellow solid (18 g, 87%).
(R)-5-(3-fluoro-2-methyl-4-phenoxyphenyl)-N-(1-(3-methoxypropanoyl)piperidin-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamide[ No CAS ]
(R)-5-(3-fluoro-2-methyl-4-phenoxyphenyl)-N-(1-(3-(methylsulfonyl)propanoyl)piperidin-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamide[ No CAS ]
(R)-5-(3-fluoro-2-methyl-4-phenoxyphenyl)-N-(1-(2-hydroxyacetyl)piperidin-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamide[ No CAS ]
(R)-5-(3-fluoro-2-methyl-4-phenoxyphenyl)-N-(1-(2-methoxyacetyl)piperidin-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamide[ No CAS ]
(R)-5-(3-fluoro-2-methyl-4-phenoxyphenyl)-N-(1-(3-hydroxypropanoyl)piperidin-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamide[ No CAS ]
1-(benzyloxy)-3-bromo-2-fluoro-4-nitrobenzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90.1%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 25℃; for 1.5h;
35.1 Step 1 : l -(Benzyloxy)-3-bromo-2-fluoro-4-nitrobenzene
To a solution of 3-bromo-l,2-difluoro-4-nitro-benzene (5 g, 21.1 mmol), tetrabutyl- ammonium hydrogen sulfate (720 mg, 2.1 mmol) and phenylmethanol (2.5 g, 23.1 mmol) in DCM (100 mL) was added 1 M sodium hydroxide solution (20 ml) dropwise. The mixture was stirred at 25 °C for 1.5 h and subsequently diluted with water. The resulting solution was extracted with ethyl acetate and the organic layers were combined. The organic extract was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica flash chromatography eluting (ethyl acetate/petroleum ether (1:4)) to afford the title compound (6.5 g, 90.1% yield) as a yellow solid. NMR (300 MHz, CD3OD) d 7.86 (dd, J= 9.2, 2.1 Hz, 1H), 7.51- .28 (m, 6H), 5.29 (s, 2H).
3-bromo-2-fluoro-N-(4-fluorobenzyl)-4-nitroaniline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
100%
With potassium carbonate In dimethyl sulfoxide at 20℃;
22 The synthesis of 3-bromo-2- II uoro-/V-( 4- II uorohenzyl )-4-ni troani I i ne (228-2):
The mixture of 228-1 (2.00 g, 8.40 mmol), 4-fluorobenzylamine (2.10 g, 16.8 mmol) and K2CO3 (3.48 g, 25.2 mmol) in DMSO (40 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water (160 mL). The resulting solid was collected by filtration and concentrated to give 228-2 (2.88 g, about 100% yield) as a solid. MS Calcd.: 342.0; MS Found: 343.2 [M + H] +.
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