تفاعل #42350
ord-13f72cbfbaea442d8cdb7ad596d52041
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1أخرىwithout further purification
- 2أخرىin the following reaction
- 3درجة الحرارةThe reaction mixture is heated
- 4درجة الحرارةat reflux for 3 h
- 5درجة الحرارةThe reaction mixture is cooled
- 6ترشيحfiltered
- 7غسيلwashed with saturated sodium bicarbonate, water, and brine
- 8تجفيفdried (sodium sulfate)
- 9ترشيحfiltered
- 10تركيزconcentrated under reduced pressure
- 11أخرىPurification by flash column chromatography (silica gel, 60% ethyl acetate/hexane)
الإجراء التجريبي
3-[(Dipropylamino)carbonyl]-5-iodobenzoic acid (12 g, 32 mmol) is dissolved in 20% methanol/benzene (480 mL), and 2M trimethylsilyldiazomethane in hexane (19 mL, 38 mmol) is added slowly. Upon completion of the addition, the solution is concentrated under reduced pressure to give methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate for use without further purification in the following reaction. To a −70° C. stirred solution of oxazole (120 mg, 1.7 mmol) in tetrahydrofuran (4 mL) is added n-butyllithium (1.6 M in hexanes, 1.2 mL, 1.9 mmol). After 30 min, zinc chloride (1 M in diethyl ether, 5.2 mL, 5.2 mmol) is added and the reaction mixture is warmed to 0° C. for 1 h. To this mixture is added a solution of methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate (643 mg, 1.6 mmol) in anhydrous tetrahydrofuran (3 mL) followed by palladium(0)tetrakis(triphenylphosphine) (80 mg, 0.07 mmol). The reaction mixture is heated at reflux for 3 h. The reaction mixture is cooled, diluted with ethyl acetate, filtered, washed with saturated sodium bicarbonate, water, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 60% ethyl acetate/hexane) provides the title compound in pure form. 1H NMR (400 MHz, CDCl3) δ 8.77 (s, 1H), 8.27 (s, 1H), 8.14 (s, 1H), 7.80 (s, 1H) 7.32 (s, 1H), 3.52 (t, 2H), 3.22 (t, 2H), 1.75 (m, 2H), 1.30 (m, 2H), 0.97 (t, 3H), 0.79 (t, 3H).