反应详情

To a solution of 3-aminophenylboronic acid (366 mg, 2.36 mmol, Aldrich Chem. Co.) and 5-bromo-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)-pyridine (560 mg, 1.57 mmol) in toluene (10 mL) was added Pd(0) (58 mg) and Na2CO3 (5 mL of a 2M solution), and the mixture was heated at reflux. The solvent was removed under vacuum, and the residue was extracted with ethyl acetate and chloroform. The organic extracts were dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate hexane 1:1 to afford to give the title compound (860 mg, 100% yield). MS (DCI/NH3) m/z 370 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 1.48 (s, 9h), 1.84-2.13 (m, 4H), 3.28-3.51 (m, 2H), 3.70-4.08 (m, 2H), 4.08-4.29 (m, 2H), 6.70-6.75 (m, 1H), 6.85-7.03 (m, 2H), 7.31-7.50 (m, 2H), 7.50-7.72 (m, 1H), 8.29 (d, J=3.0, 1H), 8.443 (br s, 1H).

1. temperaturewas heated
2. temperatureat reflux
3. customThe solvent was removed under vacuum
4. extractionthe residue was extracted with ethyl acetate and chloroform
5. dry with materialThe organic extracts were dried over MgSO4
6. concentrationconcentrated
7. customThe residue was chromatographed on a silica gel column
8. washeluting with ethyl acetate hexane 1:1
9. customto afford