Реакция #42571

Уравнение реакции

2-triethylstannyloxazole

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

→

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

Выход 27.8%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   Другоеpurged with argon
2. 2
   Другоеthe reaction mixture was degassed under reduced pressure for 15 min
3. 3
   Другоеpurged with argon
4. 4
   ТемператураThe reaction mixture was heated
5. 5
   Температураat reflux for 2 d
6. 6
   workup.ADDITIONdiluted with ethyl acetate
7. 7
   Промывкаwashed with water (3×50 mL)
8. 8
   Сушкаdried (sodium sulfate)
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    ДругоеPurification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

Методика

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).

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