반응 #1347412

반응 방정식

1,2 dibromoethane

Trimethylsilyl chloride

2-bromo-5-nitropyridine

3-iodo-azetidine-1-carboxylic acid tert-butyl ester

→

title compound

수율 71.1%

3-(5-Nitro-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester

수율 71.1%

용매

THF

THF

THF

THF

반응 조건

후처리

1. 1
   온도to cool to room temperature
2. 2
   workup.STIRRINGthe reaction mixture stirred at room temperature for 2 h
3. 3
   온도The mixture was then heated at 55° C. for 3 h
4. 4
   온도cooled to room temperature
5. 5
   기타quenched with saturated aqueous NaCl
6. 6
   추출Extraction with CH2Cl2
7. 7
   기타drying
8. 8
   여과(Na2SO4) of the organic phase, filtration and evaporation in vacuo
9. 9
   기타provided the crude material, which
10. 10
    기타was purified by flash column chromatography (heptane:ethyl acetate, 3:1)

실험 절차

Zn dust (520 mg, 7.95 mmol) was vigorously stirred in THF (2 ml) under nitrogen and 1,2 dibromoethane (84 μl, 0.97 mmol) was added. The suspension was then heated at 80° C. for 8 min and next allowed to cool to room temperature. Trimethylsilyl chloride (115 μl, 0.92 mmol) in THF (1 ml) was then added and the mixture further stirred at room temperature for 45 min. A solution of 3-iodo-azetidine-1-carboxylic acid tert-butyl ester (1.74 g, 6.14 mmol) in THF (2 ml) was then added dropwise to the solution over a period of 15 min and the reaction mixture stirred at room temperature for 2 h. Pd2(dba)3 (90 mg, 0.10 mmol) and P(2-furyl)3 (85 mg, 0.36 mmol) were then added to the mixture, followed by 2-bromo-5-nitropyridine (1.37 g, 6.74 mmol) in THF (4 ml). The mixture was then heated at 55° C. for 3 h, cooled to room temperature and quenched with saturated aqueous NaCl. Extraction with CH2Cl2, drying (Na2SO4) of the organic phase, filtration and evaporation in vacuo provided the crude material, which was purified by flash column chromatography (heptane:ethyl acetate, 3:1) to give the title compound (1.22 g, 71%) as a light yellow oil.

출처