反应详情

Pyridine (5 eq.) was added to a mixture of the title compound of Example 158 (100 mg, 0.27 mmol, 1 eq.), Cu(OAc)2 (1 eq.), phenylboronic acid (2 eq.), powered 4A molecular sieves, and dichloromethane (5 mL). After stirring at RT overnight, the reaction was diluted with diethyl ether and washed with 6N HCl solution. The aqueous layer was separated, made basic with 5N NaOH solution, and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. Purification by thin layer chromatography gave the title compound (22 mg, 18%) as an off-white solid. 1H NMR (400 MHz, d6-DMSO): δ 9.82 (s, 1H), 8.80 (d, J=2.1, 1H), 7.62 (s, 1H), 7.62 (s, 1H), 7.53–7.42 (m, 5H), 7.30–7.27 (m, 2H), 7.22–7.17 (m, 1H), 7.09 (d, J=8.0, 2H), 6.95 (d, J=7.6, 1H), 3.98 (s, 3H), 3.22 (q, J=7.3, 2H), 1.13 (t, J=7.3, 3H). MS (ES+, m/z)=451 (m+H)+.

1. washwashed with 6N HCl solution
2. customThe aqueous layer was separated
3. extractionextracted with ethyl acetate (3×20 mL)
4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customPurification by thin layer chromatography