Cesium carbonate → Tert-butyl (1r)-3-{6-chloro-5-[(e)-2-pyridin-4-ylvinyl]pyridin-3-yl}-1-(1h-indol-3-ylmethyl)propylcarbamate

A solution of Example 21C (100 mg, 0.35 mmol) in THF (3 mL) at 0° C. was treated with 9-BBN (0.5 M solution in THF, 0.70 mL, 0.35 mmol), stirred overnight while gradually warming to room temperature, cannulated into a mixture of Example 21B (108 mg, 0.32 mmol), PdCl2 (dppf) (26 mg, 0.032 mmol) and Cs2CO3 (228 mg, 0.7 mmol) in DMF, purged with nitrogen, and stirred at 50° C. for 8 hours. The mixture was treated with ethyl acetate (50 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The residual oil was purified by flash column chromatography on silica gel with 80% ethyl acetate/hexanes to provide the desired product (69 mg, 40%).

1. custompurged with nitrogen
2. stirringstirred at 50° C. for 8 hours
3. additionThe mixture was treated with ethyl acetate (50 mL)
4. washwashed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residual oil was purified by flash column chromatography on silica gel with 80% ethyl acetate/hexanes

ORDレコード

ord-c07dbc26b4754398881ea11c3dfa415d

出典データセット

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06831175B2