تفاعل #42571

معادلة التفاعل

2-triethylstannyloxazole

methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate

→

methyl 3-[(dipropylamino)carbonyl]-5-(1,3-oxazol-2-yl)benzoate

المردود 27.8%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىpurged with argon
2. 2
   أخرىthe reaction mixture was degassed under reduced pressure for 15 min
3. 3
   أخرىpurged with argon
4. 4
   درجة الحرارةThe reaction mixture was heated
5. 5
   درجة الحرارةat reflux for 2 d
6. 6
   workup.ADDITIONdiluted with ethyl acetate
7. 7
   غسيلwashed with water (3×50 mL)
8. 8
   تجفيفdried (sodium sulfate)
9. 9
   تركيزconcentrated under reduced pressure
10. 10
    أخرىPurification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

الإجراء التجريبي

A stirred solution of 2-triethylstannyloxazole (Chem. Mater. 1994, 6, 1023) (1.5 g, 5.5 mmol) and methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate (1.8 g, 4.6 mmol) in dimethylformamide (12 mL) was degassed under reduced pressure for 15 min and purged with argon. Palladium(0)tetrakis(triphenylphosphine) (158 mg, 0.14 mmol) was added and the reaction mixture was degassed under reduced pressure for 15 min and then purged with argon. The reaction mixture was heated at reflux for 2 d, cooled to room temperature, diluted with ethyl acetate, washed with water (3×50 mL), dried (sodium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes) provided methyl 3-[(dipropylamino)carbonyl]-5-(1,3-oxazol-2-yl)benzoate (423 mg): 1H NMR (300 MHz, CDCl3) δ 8.73 (s, 1H), 8.23 (s, 1H), 8.11 (s, 1H), 7.76 (s, 1H), 7.28 (s, 1H), 3.97 (s, 3H), 3.49 (br s, 2H), 3.18 (br s, 2H), 1.72 (d, J=7 Hz, 2H), 1.55 (d, J=7 Hz, 2H), 1.00 (t, J=7 Hz, 3H), 0.75 (t, J=7 Hz, 3H).

المصدر