反应详情

To a solution of (3-(tert-butyldimethylsilyloxy)azetidin-1-yl)(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)methanone 273 (336 mg, 0.67 mmol) and NiCl2.6H2O (318 g, 1.34 mmol) in MeOH/THF (4.7 mL/4.7 mL) was added NaBH4 (101 g, 2.68 mmol) at 0° C. and the mixture stirred for 1 hr. The reaction mixture was added to an EDTA.4Na (1.1 g/100 mL) solution and extracted with EtOAc. The aqueous layer was filtered and extracted again with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (pure EtOAc) giving 274 as creamy foam (145.2 mg, 46% yield). MS (m/z): (M+1) 474.1 (100%).

1. extraction4Na (1.1 g/100 mL) solution and extracted with EtOAc
2. filtrationThe aqueous layer was filtered
3. extractionextracted again with EtOAc
4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by flash chromatography (pure EtOAc)