تفاعل #974963

معادلة التفاعل

methyl 3-amino-6-bromo-5-fluoro-2-methylbenzoate

sodium nitrite

→

title compound

المردود 52.0%

methyl 5-bromo-6-fluoro-1H-indazole-4-carboxylate

المردود 52.0%

المذيبات

acetic acid

water

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated under reduced pressure
2. 2
   workup.ADDITIONThe residue was diluted with ethyl acetate
3. 3
   غسيلwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   أخرىThe solvent was evaporated under reduced pressure
6. 6
   أخرىthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→40/60)

الإجراء التجريبي

To a solution of methyl 3-amino-6-bromo-5-fluoro-2-methylbenzoate (1.33 g, 5.09 mmol) in acetic acid (25 mL) heated to 50° C. was added a solution of sodium nitrite (369 mg, 5.34 mmol) in water (1 mL), and the mixture was stirred for 1.5 hr and concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→40/60) to give the title compound (700 mg, yield 52%).

المصدر