反应详情

温度

65 °C

A mixture of 3-bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (042 g, 1.24 mmol) (from Example 1 supra), 3-(2-methyl-2H-tetrazol-5-yl)-phenol (0.23 g, 1.31 mmol) (from Example 30 supra), potassium iodide (0.21 g, 1.24 mmol), potassium carbonate (0.38 g, 2.78 mmol) and 18-crown-6 (16.0 mg, 0.06 mmol) in N,N-dimethylformamide (15 mL) was heated at 65° C. for 1 day. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phase washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 30% ethyl acetate in hexanes to give 4-chloro-3-[3-(2-methyl-2H-tetrazol-5-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester. (Yield 0.15 g, 28%).

1. customThe reaction mixture was partitioned between ethyl acetate and water
2. extractionThe aqueous phase was extracted with ethyl acetate (2×)
3. washThe combined organic phase washed with water and brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe residue was purified by flash chromatography
7. washeluting with 30% ethyl acetate in hexanes