반응 #42571

반응 방정식

2-triethylstannyloxazole

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

→

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

수율 27.8%

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타purged with argon
2. 2
   기타the reaction mixture was degassed under reduced pressure for 15 min
3. 3
   기타purged with argon
4. 4
   온도The reaction mixture was heated
5. 5
   온도at reflux for 2 d
6. 6
   workup.ADDITIONdiluted with ethyl acetate
7. 7
   세척washed with water (3×50 mL)
8. 8
   건조dried (sodium sulfate)
9. 9
   농축concentrated under reduced pressure
10. 10
    기타Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

실험 절차

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).

출처