反应详情

温度

110 °C

3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)benzyl 1-[3-({[tert-butyl(diphenyl)silyl]oxy}methyl)benzyl]-5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate (2.18 g, 2.38 mmol, from Step 3) and di-tert-butyl hydrazine-1,2-dicarboxylate (0.71 g, 3.1 mmol, Aldrich), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine-(2′-aminobiphenyl-2-yl)(chloro)palladium (1:1) (0.22 g, 0.28 mmol, Aldrich) and Cs2CO3 (0.91 g, 2.8 mmol) were combined in toluene (27 mL) and the mixture was degassed by a stream of nitrogen bubbled through the solution for 10 minutes. The reaction vessel was sealed and heated at 110° C. for 3 hours. The reaction mixture was partitioned between water and ethyl acetate, the aqueous layer was extracted three times and the combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-25% EtOAc/hexanes. Yield: (1.31 g, 50%).

1. customthe mixture was degassed by a stream of nitrogen
2. custombubbled through the solution for 10 minutes
3. customThe reaction vessel was sealed
4. customThe reaction mixture was partitioned between water and ethyl acetate
5. extractionthe aqueous layer was extracted three times
6. dry with materialthe combined organic extracts were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe product was purified by flash chromatography
10. washeluting with a gradient from 0-25% EtOAc/hexanes